GB921536A - Substituted n-hydroxyureas and a process for their manufacture - Google Patents
Substituted n-hydroxyureas and a process for their manufactureInfo
- Publication number
- GB921536A GB921536A GB5753/61A GB575361A GB921536A GB 921536 A GB921536 A GB 921536A GB 5753/61 A GB5753/61 A GB 5753/61A GB 575361 A GB575361 A GB 575361A GB 921536 A GB921536 A GB 921536A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- hydroxyurea
- chloride
- formula
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 20
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 5
- 229910052794 bromium Inorganic materials 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- MTFFANYLEXKMTD-UHFFFAOYSA-N 1-hydroxy-1-phenylurea Chemical compound NC(=O)N(O)C1=CC=CC=C1 MTFFANYLEXKMTD-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000005442 diisocyanate group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000012948 isocyanate Substances 0.000 abstract 2
- 150000002513 isocyanates Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- CQFAZYIIBJEZEA-UHFFFAOYSA-N 1-(2-ethylhexyl)-1-hydroxyurea Chemical compound C(C)C(CN(C(=O)N)O)CCCC CQFAZYIIBJEZEA-UHFFFAOYSA-N 0.000 abstract 1
- GUXVTBWCFWLEIH-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-hydroxyurea Chemical compound NC(=O)N(O)C1=CC=CC(Cl)=C1 GUXVTBWCFWLEIH-UHFFFAOYSA-N 0.000 abstract 1
- XTMHRZWPZIGSAS-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-1-hydroxyurea Chemical compound C(C)OC1=CC=C(C=C1)N(C(=O)N)O XTMHRZWPZIGSAS-UHFFFAOYSA-N 0.000 abstract 1
- SIFUJPAPFQGARI-UHFFFAOYSA-N 1-cyclooctyl-1-hydroxyurea Chemical compound C1(CCCCCCC1)N(C(=O)N)O SIFUJPAPFQGARI-UHFFFAOYSA-N 0.000 abstract 1
- OLGRHUYOZJKXFC-UHFFFAOYSA-N 1-ethenyl-1-hydroxyurea Chemical compound C(=C)N(C(=O)N)O OLGRHUYOZJKXFC-UHFFFAOYSA-N 0.000 abstract 1
- FHDKVJQMGSAZGU-UHFFFAOYSA-N 1-hydroxy-1-(3-methylphenyl)urea Chemical compound C1(=CC(=CC=C1)N(C(=O)N)O)C FHDKVJQMGSAZGU-UHFFFAOYSA-N 0.000 abstract 1
- WPGSGRPEYCWSBJ-UHFFFAOYSA-N 1-hydroxy-1-(4-methylphenyl)sulfonylurea Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)N)O)C WPGSGRPEYCWSBJ-UHFFFAOYSA-N 0.000 abstract 1
- CQRLSPHZAITAOI-UHFFFAOYSA-N 1-hydroxy-1-(4-methylphenyl)urea Chemical compound CC1=CC=C(N(O)C(N)=O)C=C1 CQRLSPHZAITAOI-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000008422 chlorobenzenes Chemical class 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- -1 hydroxycarbamyl Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004957 naphthylene group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1836—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid
- C07C273/1845—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid comprising the -N-C(O)-Hal moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds (excepting N-phenyl-N1-hydroxyurea) of the general formulae <FORM:0921536/IV(a)/1> and <FORM:0921536/IV(a)/2 may be mono-, di- or tri-substituted by alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 3 carbon atoms, alkoxy contain1 to 2 carbon atoms, chlorine or bromine; alkyl containing 1 to 8 carbon atoms; aralkyl containing 1 carbon atom in the alkyl component; halogenalkyl in which the halogen is chlorine or bromine and which contains 1 to 4 carbon atoms; halogenaralkyl in which the halogen is chlorine or bromine and which contains 1 or 2 carbon atoms in the alkyl component; cyanoalkyl containing 1 to 4 carbon atoms; cyanoaralkyl containing 1 to 2 carbon atoms in the alkyl component; cycloalkyl containing 6 to 8 carbon atoms as ring members; alkenyl containing 2 to 3 carbon atoms; alkinyl containing 3 to 5 carbon atoms; halogenalkinyl containing 3 to 5 carbon atoms or a radical of the formula <FORM:0921536/IV(a)/3> wherein X represents hydrogen, methyl, chloromethyl, bromine or methoxyl and n is 1 or 2; R1 stands for phenylene or naphthylene which may be mono-, di- or tri-substituted by alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 3 carbon atoms, chlorine or bromine; alkylene containing 2 to 8 carbon atoms; aralkylene containing 1 to 2 carbon atoms in the alkylene component; radicals of the formulae <FORM:0921536/IV(a)/4> or <FORM:0921536/IV(a)/5> or cycloalkylene containing 6 to 8 carbon atoms as ring members; R11 stands for hydrogen; alkyl containing 1 to 8 carbon atoms; hydroxyalkyl containing 1 to 8 carbon atoms; or alkenyl containing 3 carbon atoms. The invention also comprises a process for preparing the said compounds (including N-phenyl-N1-hydroxyurea) wherein 1 mol of an isocyanate of formula R-R=C=O or of a carbamyl chloride of formula <FORM:0921536/IV(a)/6> or 1/2 mol of a diisocyanate of formula O=C=N-R1-N=C=O or of a dicarbamyl chloride of formula <FORM:0921536/IV(a)/7> is added to 1 to 3 mols of a hydroxylamine of formula R11-NHOH at a temperature between 0 DEG to 70 DEG C. in the presence of water and of an organic solvent which reacts neither with the isocyanate, diisocyanate, carbamyl chloride or dicarbamyl chloride nor with the hydroxylamine and, if a carbamyl chloride or a dicarbamyl chloride is used as starting material, in the presence of an acid-binding substance, R, R1 and R11 having the same meanings as stated above. The reaction is advantageously carried out in the presence of a substance which is capable of forming complex compounds with metals, e.g. ethylenediaminotetraacetic acid or one of its salts. Suitable solvents for the process include diethyl ether, b ,b 1-dichlorodiethyl ether, toluene, methylene chloride, chlorobenzenes, acetonitrile, dioxan, tetrahydrofuran and dimethyl sulphoxide as typical examples of those specified. Mixtures of these solvents may also be used. The hydroxylamine is reacted in free form and is preferably liberated from one of its salts, e.g. the chloride, sulphite or acetate, by means of aqueous, alkaline solution. Examples illustrate the preparation of inter alia N-p-ethoxyphenyl-N1-hydroxyurea, N-p-tolyl-N1-hydroxyurea, N-m-chlorophenyl-N1-hydroxyurea, N - (2 - ethylhexyl)-N1-hydroxyurea, N-(g -chloropropyl)-N1-hydroxyurea, N-cyclooctyl - N1 - hydroxyurea, N - vinyl - N1 - hydroxyurea, N-phenyl-N1-ethyl-N1-hydroxyurea, N,N1-bis(hydroxycarbamyl)-naphthylene-1,5-diamine, N,N1-bis(N11-methyl-N11-hydroxy-carbamyl) - toluylene - 2,4 - diamine and N-p-toluenesulphonyl - N1 - hydroxyurea. The N-hydroxyureas can be alkylated by conventional means; for example, N-m-tolyl-N1-methyl-N1-methoxyurea is obtained by treating N-m-tolyl-N1-hydroxyurea with dimethyl sulphate. The N-hydroxyureas can be used as intermediates for the production of pharmaceuticals or plant protection agents.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB56710A DE1127344B (en) | 1960-02-18 | 1960-02-18 | Process for the preparation of N-aryl-N'-hydroxyureas |
| DEB58874A DE1131655B (en) | 1960-08-05 | 1960-08-05 | Process for the production of urea derivatives |
| DEB59003A DE1129151B (en) | 1960-08-17 | 1960-08-17 | Process for the production of substituted ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB921536A true GB921536A (en) | 1963-03-20 |
Family
ID=27209105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5753/61A Expired GB921536A (en) | 1960-02-18 | 1961-02-16 | Substituted n-hydroxyureas and a process for their manufacture |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE600278A (en) |
| GB (1) | GB921536A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4534911A (en) * | 1982-12-13 | 1985-08-13 | Continental Pharma, Inc. | Method for the preparation of p-butoxyphenylacetyl-hydroxamic acid in the finely divided state and a composition containing this acid |
| US5036157A (en) * | 1986-03-11 | 1991-07-30 | Burroughs Wellcome Co. | Aryl derivatives |
| US5559144A (en) * | 1990-07-25 | 1996-09-24 | Abbott Laboratories | Furyl and thienyl alkynyl-N-hydroxy urea derivatives |
| US8512464B2 (en) | 2009-12-02 | 2013-08-20 | 3M Innovative Properties Company | Functionalized zirconia nanoparticles and high index films made therefrom |
| CN105330570A (en) * | 2015-11-05 | 2016-02-17 | 齐鲁天和惠世制药有限公司 | Preparing method for hydroxyurea |
-
1961
- 1961-02-16 BE BE600278A patent/BE600278A/en unknown
- 1961-02-16 GB GB5753/61A patent/GB921536A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4534911A (en) * | 1982-12-13 | 1985-08-13 | Continental Pharma, Inc. | Method for the preparation of p-butoxyphenylacetyl-hydroxamic acid in the finely divided state and a composition containing this acid |
| US5036157A (en) * | 1986-03-11 | 1991-07-30 | Burroughs Wellcome Co. | Aryl derivatives |
| US5559144A (en) * | 1990-07-25 | 1996-09-24 | Abbott Laboratories | Furyl and thienyl alkynyl-N-hydroxy urea derivatives |
| US8512464B2 (en) | 2009-12-02 | 2013-08-20 | 3M Innovative Properties Company | Functionalized zirconia nanoparticles and high index films made therefrom |
| US8569537B2 (en) | 2009-12-02 | 2013-10-29 | 3M Innovative Properties Company | Functionalized zirconia nanoparticles and high index films made therefrom |
| CN105330570A (en) * | 2015-11-05 | 2016-02-17 | 齐鲁天和惠世制药有限公司 | Preparing method for hydroxyurea |
Also Published As
| Publication number | Publication date |
|---|---|
| BE600278A (en) | 1961-08-16 |
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