GB599178A - Thiolcarbamic esters - Google Patents
Thiolcarbamic estersInfo
- Publication number
- GB599178A GB599178A GB2568445A GB2568445A GB599178A GB 599178 A GB599178 A GB 599178A GB 2568445 A GB2568445 A GB 2568445A GB 2568445 A GB2568445 A GB 2568445A GB 599178 A GB599178 A GB 599178A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenylthiolcarbamate
- thiolcarbamate
- ethyl
- bis
- sodium
- 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
- 150000002148 esters Chemical class 0.000 title abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 8
- IOODZBQYPMVNIG-UHFFFAOYSA-N C1(=CC=CC=C1)OC(NC=1SC=CC1)=O.[Na] Chemical compound C1(=CC=CC=C1)OC(NC=1SC=CC1)=O.[Na] IOODZBQYPMVNIG-UHFFFAOYSA-N 0.000 abstract 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N Allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 3
- XXYKHOWJGCAXNA-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCC Chemical compound C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCC XXYKHOWJGCAXNA-UHFFFAOYSA-N 0.000 abstract 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N N-Propyl bromide Chemical group CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 3
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical group CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 2
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 abstract 2
- IVOBXIMQZLYEJI-UHFFFAOYSA-L S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)[O-])NC(=O)[O-].[Na+].[Na+] Chemical compound S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)[O-])NC(=O)[O-].[Na+].[Na+] IVOBXIMQZLYEJI-UHFFFAOYSA-L 0.000 abstract 2
- -1 alkaline-earth metal salt Chemical class 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-Dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-Dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 abstract 1
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 abstract 1
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 abstract 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 abstract 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Nitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- QBEAPWZQCQPICI-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)C1=C(SC=C1)NC(=O)OC Chemical compound C(CCCCCCCCCCCCCCCCC)C1=C(SC=C1)NC(=O)OC QBEAPWZQCQPICI-UHFFFAOYSA-N 0.000 abstract 1
- PKBDXCYUWJZONB-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)OC(NC=1SC=CC1)=O.[Na] Chemical compound C(CCCCCCCCCCCCCCCCC)OC(NC=1SC=CC1)=O.[Na] PKBDXCYUWJZONB-UHFFFAOYSA-N 0.000 abstract 1
- VOIUPNFLOVTDEC-UHFFFAOYSA-L C1(=CC(=CC=C1)C1=C(SC=C1)NC(=O)[O-])C1=C(SC=C1)NC(=O)[O-] Chemical compound C1(=CC(=CC=C1)C1=C(SC=C1)NC(=O)[O-])C1=C(SC=C1)NC(=O)[O-] VOIUPNFLOVTDEC-UHFFFAOYSA-L 0.000 abstract 1
- WXUGFMYNZXLUDA-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)[N+](=O)[O-] Chemical compound C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)[N+](=O)[O-] WXUGFMYNZXLUDA-UHFFFAOYSA-N 0.000 abstract 1
- JCEWYIWAEDNUGI-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCC(=O)OCC Chemical compound C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCC(=O)OCC JCEWYIWAEDNUGI-UHFFFAOYSA-N 0.000 abstract 1
- LMNHVOGZHNAICC-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCCCCCCCCCCCCCCCC Chemical compound C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OCCCCCCCCCCCCCCCC LMNHVOGZHNAICC-UHFFFAOYSA-N 0.000 abstract 1
- JBSXROVWAHTRPI-UHFFFAOYSA-N C1(=CC=CC=C1)OC(NC=1SC=CC1)=O.[Ca] Chemical compound C1(=CC=CC=C1)OC(NC=1SC=CC1)=O.[Ca] JBSXROVWAHTRPI-UHFFFAOYSA-N 0.000 abstract 1
- YKCSONFYTQHTKO-UHFFFAOYSA-N C1(CCCCC1)C1=C(SC=C1)NC(=O)OC Chemical compound C1(CCCCC1)C1=C(SC=C1)NC(=O)OC YKCSONFYTQHTKO-UHFFFAOYSA-N 0.000 abstract 1
- XCVQDFLWRSHPLJ-UHFFFAOYSA-N C1(CCCCC1)OC(NC=1SC=CC1)=O.[Na] Chemical compound C1(CCCCC1)OC(NC=1SC=CC1)=O.[Na] XCVQDFLWRSHPLJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N Chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 abstract 1
- OKNKOQLXHINJQJ-UHFFFAOYSA-N S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)OCC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1 Chemical compound S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)OCC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1 OKNKOQLXHINJQJ-UHFFFAOYSA-N 0.000 abstract 1
- DUUSULCXXQZPNT-UHFFFAOYSA-N S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)OCCC)NC(=O)OCCC Chemical compound S1C(=C(C=C1)CCCCCCC1=C(SC=C1)NC(=O)OCCC)NC(=O)OCCC DUUSULCXXQZPNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical group COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 1
- NMCTUHZAVTWCQR-UHFFFAOYSA-N phenyl N-thiophen-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC=CS1 NMCTUHZAVTWCQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 abstract 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Thiolcarbamic esters, of the general formula R(NHCOSR1)n, wherein R and R1 represent hydrocarbon radicals, substituted or unsubstituted, the same or different, and n is 1, 2 or 3, are manufactured by treating an alkali or alkaline-earth metal salt of a thiolcarbamic acid R(NHCOSH)n, advantageously in the presence of a solvent, with a substance capable of replacing alkali or alkaline earth metal by an organic radical or radicals, e.g. a substance containing one or more reactive halogen atoms, -SO4 groups (as in dialkyl sulphates) or -SO3 Aryl groups (as in alkyl toluenesulphonates). In examples: (1) sodium phenylthiolcarbamate is stirred with dimethyl or diethyl sulphate in aqueous solution at 0 DEG C. to produce methyl or ethyl phenylthiolcarbamate; (2) sodium cyclohexylthiolcarbamate and dimethyl sulphate similarly yield methyl cyclohexylthiolcarbamate; (3) sodium octadecylthiolcarbamate is heated with dimethyl sulphate in toluene to form methyl octadecylthiolcarbamate; (4) benzyl chloride is stirred with an aqueous solution of disodium hexamethylenebis-(thiolcarbamate) to give dibenzyl hexamethylene-bis-(thiolcarbamate); (5) sodium phenylthiolcarbamate is stirred with ethyl bromide in ethyl alcohol, producing ethyl phenylthiolcarbamate; the ethyl bromide may be replaced by n-propyl, n-butyl or allyl bromide or methallyl chloride; (6) cetyl bromide similarly yields cetyl phenylthiolcarbamate; (7) ethyl chloracetate similarly gives carbethoxymethyl phenylthiolcarbamate; (8) disodium hexamethylene - bis - (thiolcarbamate) and n-propyl bromide similarly yield dipropyl hexamethylene-bis-(thiolcarbamate); the n-propyl bromide may be replaced by ethyl, n-butyl or allyl bromide or methallyl chloride; (9) disodium p : p1-diphenyl-bis-(thiolcarbamate) and allyl bromide similarly give diallyl p : p1-diphenyl-bis-(thiolcarbamate); (10) disodium p : p1 - diphenylmethane - bis - (thiolcarbamate) similarly yields diallyl p : p1-diphenylmethane-bis-(thiolcarbamate); (11) calcium phenylthiolcarbamate is stirred with chloracetamide in aqueous solution to produce carbamylmethyl phenylthiolcarbamate; (12) sodium phenylthiolcarbamate is stirred with methyl or ethyl p-toluenesulphonate in ethyl alcohol at 0-5 DEG C. to form methyl or p ethyl phenylthiolcarbamate; (13) sodium phenylthiolcarbamate is heated with p-chloronitrobenzene to produce p-nitrophenyl phenylthiolcarbamate. Additional starting materials specified are, on the one hand, disodium m - phenylene - bis - (thiolcarbamate) and trisodium 1 : 3 : 5 - triethylbenzene-2 : 4 : 6-tris-(thiolcarbamate), and, on the other hand, ethylene dibromide, trimethylene dibromide, ethylene chlorobromide and p-xylylene dichloride. Alkali and alkaline-earth metal thiolcarbamates are obtainable by treating the corresponding isocyanates with alkali or alkaline-earth metal hydrosulphides. Specification 599,177 is referred to in the Provisional Specification.
Publications (1)
Publication Number | Publication Date |
---|---|
GB599178A true GB599178A (en) | 1948-03-05 |
Family
ID=1739422
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2568445A Expired GB599178A (en) | 1945-10-03 | Thiolcarbamic esters |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB599178A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2852361A (en) * | 1954-02-24 | 1958-09-16 | Monsanto Chemicals | Method of defoliating plants with alkylenebis |
DE1136693B (en) * | 1958-09-18 | 1962-09-20 | Bayer Ag | Process for the preparation of basic substituted thiolcarbamic acid alkyl esters |
DE1149709B (en) * | 1960-04-07 | 1963-06-06 | Bayer Ag | Process for the preparation of basic substituted phenylthiocarbamic acid S-alkyl esters |
-
1945
- 1945-10-03 GB GB2568445A patent/GB599178A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2852361A (en) * | 1954-02-24 | 1958-09-16 | Monsanto Chemicals | Method of defoliating plants with alkylenebis |
DE1136693B (en) * | 1958-09-18 | 1962-09-20 | Bayer Ag | Process for the preparation of basic substituted thiolcarbamic acid alkyl esters |
DE1149709B (en) * | 1960-04-07 | 1963-06-06 | Bayer Ag | Process for the preparation of basic substituted phenylthiocarbamic acid S-alkyl esters |
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