GB1092134A - Production of carbamyl halides - Google Patents
Production of carbamyl halidesInfo
- Publication number
- GB1092134A GB1092134A GB940265A GB940265A GB1092134A GB 1092134 A GB1092134 A GB 1092134A GB 940265 A GB940265 A GB 940265A GB 940265 A GB940265 A GB 940265A GB 1092134 A GB1092134 A GB 1092134A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- methylcarbamyl
- carbamyl
- methyl
- denotes
- 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
- -1 carbamyl halides Chemical class 0.000 title abstract 7
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- FSBLIZXPIXHWML-UHFFFAOYSA-N n-(chloromethyl)-n-methylcarbamoyl chloride Chemical compound ClCN(C)C(Cl)=O FSBLIZXPIXHWML-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- AWESKXAOZNSPDT-UHFFFAOYSA-N N,N-bis(methoxymethyl)carbamoyl chloride Chemical compound COCN(C(=O)Cl)COC AWESKXAOZNSPDT-UHFFFAOYSA-N 0.000 abstract 1
- DVUUQHWMBZHFGD-UHFFFAOYSA-N N-(3,5-dichloro-3,5-dimethylmorpholin-4-yl)carbamoyl chloride Chemical compound ClC1(N(C(COC1)(C)Cl)NC(=O)Cl)C DVUUQHWMBZHFGD-UHFFFAOYSA-N 0.000 abstract 1
- OIDVLUUSNQDXEC-UHFFFAOYSA-N N-(3,5-dimethoxy-3,5-dimethylmorpholin-4-yl)carbamoyl chloride Chemical compound COC1(N(C(COC1)(C)OC)NC(=O)Cl)C OIDVLUUSNQDXEC-UHFFFAOYSA-N 0.000 abstract 1
- LWRJTNNWKFEFAD-UHFFFAOYSA-N N-(benzylsulfanylmethyl)-N-methylcarbamoyl chloride Chemical compound C(C1=CC=CC=C1)SCN(C(=O)Cl)C LWRJTNNWKFEFAD-UHFFFAOYSA-N 0.000 abstract 1
- DISZHTAQHBQAGZ-UHFFFAOYSA-N N-(cyclohexyloxymethyl)-N-methylcarbamoyl chloride Chemical compound C1(CCCCC1)OCN(C(=O)Cl)C DISZHTAQHBQAGZ-UHFFFAOYSA-N 0.000 abstract 1
- XOKTYFAAPHPDGN-UHFFFAOYSA-N N-methyl-N-(prop-1-enoxymethyl)carbamoyl chloride Chemical compound C(=CC)OCN(C(=O)Cl)C XOKTYFAAPHPDGN-UHFFFAOYSA-N 0.000 abstract 1
- CNNBSCAATUKVPS-UHFFFAOYSA-N N-methyl-N-(prop-1-ynoxymethyl)carbamoyl chloride Chemical compound C(#CC)OCN(C(=O)Cl)C CNNBSCAATUKVPS-UHFFFAOYSA-N 0.000 abstract 1
- QCIVYYCDPFJFLR-UHFFFAOYSA-N N-methyl-N-(propan-2-yloxymethyl)carbamoyl chloride Chemical compound C(C)(C)OCN(C(=O)Cl)C QCIVYYCDPFJFLR-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- KGXGPHUJJBHGDL-UHFFFAOYSA-N n,n-bis(chloromethyl)carbamoyl chloride Chemical compound ClCN(CCl)C(Cl)=O KGXGPHUJJBHGDL-UHFFFAOYSA-N 0.000 abstract 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 abstract 1
- QNXQVLFWRVUENR-UHFFFAOYSA-N n-(methoxymethyl)-n-methylcarbamoyl chloride Chemical compound COCN(C)C(Cl)=O QNXQVLFWRVUENR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/04—Carbamic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to disubstituted carbamyl halides of the formula <FORM:1092134/C2/1> in which R1 to R4 denote identical or different hydrogen atoms or alkyl, aralkyl or aryl radicals, or R2 and R3 when joined together form an alkylene radical (R2 and R3 having 2-5 carbon atoms) in which one methylene group may be replaced by an oxygen or sulphur atom or a group > NR7, in which R7 denotes an alkyl, cycloalkyl or phenyl radical, X denotes chlorine or bromine, Y denotes hydrogen or a radical -ZR5, Z denotes oxygen or sulphur, and R5 denotes an unsubstituted or substituted alkyl, alkenyl, alkynyl, aralkyl, aryl, alkaryl or cycloalkyl radical or a radical -(Z:)CR6, in which R6 denotes an unsubstituted or substituted alkyl, alkenyl, alkynyl, aralkyl, aryl, alkaryl or cycloalkyl radical. The compounds are obtainable by reacting a carbamyl halide of the formula <FORM:1092134/C2/2> in which B denotes hydrogen or a chlorine or bromine atom, with a compound of the formula HZR5 or an alkali or alkaline-earth metal salt thereof at -40 DEG to 120 DEG C., optionally in an organic solvent. Specified reactants of the second formula above include N-chloromethyl-methylcarbamyl chloride, N,N - bis(chloromethyl)carbamyl chloride, N - a - chlorobenzyl - N - chloromethylcarbamyl chloride, N - (a - chloromorpholyl)carbamyl chloride and N(a ,a 1 - dichlorothiomorpholyl)carbamyl chloride. A number of alcohols, phenols or mercaptans which may constitute the reactant HZR5 are specified. Also specified are a number of carboxylic and thiocarboxylic acids which may be used when HZR5 has the value HZ(Z:)CR6. In typical examples, (1) N-chloromethyl - N - methylcarbamyl chloride and sodium methylate yield N-methoxymethyl-N-methylcarbamyl chloride, (2) N-bis(chloro-methyl)carbamyl chloride and sodium methylate yield N,N-bis(methoxy methyl)carbamyl chloride, (3) N-(3,5-dichloro-3,5-dimethylmorpholyl)carbamyl chloride and sodium methylate yield N - (3,5 - dimethoxy - 3,5 - dimethylmorpholyl)carbamyl chloride, (4) N-(a -chloroethyl)-N-methylcarbamyl chloride and acetic acid yield N - (a - acetoxyethyl) - N - methylcarbamyl chloride, and (5) N-methyl-N-chloromethylcarbamyl chloride and methyl mercaptan yield N - methyl - N - methylthiocarbamyl chloride. Other specified products include N-methyl-N-(2-ethylhexoxymethyl carbamyl chloride, N-isopropoxymethyl-N-methylcarbamyl chloride, N - propynoxymethyl - N - methylcarbamyl chloride, N - (1 - methylpropyne - (2) - oxymethyl) - N - methylcarbamyl chloride, N - propeneoxymethyl - N - methyl carbamyl chloride, N - (b - ethoxyethoxymethyl) - N - methylcarbamyl chloride, N - (b - bromo-ethoxymethyl) - N - methylcarbamyl chloride, N - cyclohexoxymethyl - N - methylcarbamyl chloride, N - (b - phenylethoxymethyl) - N - methylcarbamyl chloride, N - (a - methoxypiperidyl)carbamyl chloride, N - (a - propionyl-oxymethyl) - N - methylcarbamyl chloride, N,N - bis(a - acetoxymethyl)carbamyl chloride, N - (a - acryloxymethyl) - N - methylcarbamyl chloride, N - acetothiomethyl - N - methylcarbamyl chloride, N - benzylthiomethyl - N - methylcarbamyl chloride, and N - (a - methylthiomorpholyl)carbamyl chloride.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75782A DE1232946B (en) | 1964-03-07 | 1964-03-07 | Process for the preparation of aethercarbamic acid halides |
| DEB0078823 | 1964-10-07 | ||
| DEB80076A DE1253698B (en) | 1965-01-12 | 1965-01-12 | Process for the preparation of thioether carbamic acid halides |
| DEB80146A DE1253699B (en) | 1965-01-16 | 1965-01-16 | Process for the preparation of acyloxycarbamic acid halides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1092134A true GB1092134A (en) | 1967-11-22 |
Family
ID=27436628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB940265A Expired GB1092134A (en) | 1964-03-07 | 1965-03-05 | Production of carbamyl halides |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT256875B (en) |
| BE (1) | BE660727A (en) |
| CH (1) | CH449601A (en) |
| FR (1) | FR1432865A (en) |
| GB (1) | GB1092134A (en) |
| NL (1) | NL6502858A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3025778A4 (en) * | 2013-07-25 | 2017-03-29 | Showa Denko K.K. | Reaction accelerator, urethane compound using same, thiourethane compound, and production method for amide compound or urea compound |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2826012A1 (en) * | 1978-06-14 | 1980-01-03 | Basf Ag | NEW BIS- (N-HALOGENMETHYL) -CARBAMID ACID ESTERS AND METHOD FOR THE PRODUCTION THEREOF |
| JP4749579B2 (en) * | 2000-04-17 | 2011-08-17 | 昭和電工株式会社 | (Meth) acryloyl group-containing carbamic acid halides and method for producing the same |
| US6646156B2 (en) * | 2000-04-17 | 2003-11-11 | Showa Denko Kabushiki Kaisha | (Meth)acryloyl-group-containing carbamoyl halides and production process therefor |
-
1965
- 1965-03-03 CH CH291865A patent/CH449601A/en unknown
- 1965-03-05 BE BE660727D patent/BE660727A/xx unknown
- 1965-03-05 NL NL6502858A patent/NL6502858A/xx unknown
- 1965-03-05 GB GB940265A patent/GB1092134A/en not_active Expired
- 1965-03-08 FR FR8271A patent/FR1432865A/en not_active Expired
- 1965-03-08 AT AT202565A patent/AT256875B/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3025778A4 (en) * | 2013-07-25 | 2017-03-29 | Showa Denko K.K. | Reaction accelerator, urethane compound using same, thiourethane compound, and production method for amide compound or urea compound |
| US9656952B2 (en) | 2013-07-25 | 2017-05-23 | Showa Denko K.K. | Reaction accelerator and method of producing urethane compound, thiourethane compound, amide compound, or urea compound using same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1432865A (en) | 1966-03-25 |
| AT256875B (en) | 1967-09-11 |
| NL6502858A (en) | 1965-09-08 |
| BE660727A (en) | 1965-09-06 |
| CH449601A (en) | 1968-01-15 |
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