GB599179A - Thiolcarbamic esters - Google Patents
Thiolcarbamic estersInfo
- Publication number
- GB599179A GB599179A GB2568545A GB2568545A GB599179A GB 599179 A GB599179 A GB 599179A GB 2568545 A GB2568545 A GB 2568545A GB 2568545 A GB2568545 A GB 2568545A GB 599179 A GB599179 A GB 599179A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tolyl
- acid
- thiolchloroformate
- thiolcarbamate
- bis
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- 239000011230 binding agent Substances 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000011780 sodium chloride Substances 0.000 abstract 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- QCMHWZUFWLOOGI-UHFFFAOYSA-N S-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 150000003141 primary amines Chemical class 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N Benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 abstract 1
- IEMYQZBNAOSZSB-UHFFFAOYSA-N C(C)C1=C(C(=C(C=C1)C(C1=CC=CC=C1)C1=CC=CC=C1)CC)CC Chemical compound C(C)C1=C(C(=C(C=C1)C(C1=CC=CC=C1)C1=CC=CC=C1)CC)CC IEMYQZBNAOSZSB-UHFFFAOYSA-N 0.000 abstract 1
- GPTPTPVXLBXJDP-UHFFFAOYSA-N C(CC1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C Chemical compound C(CC1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C GPTPTPVXLBXJDP-UHFFFAOYSA-N 0.000 abstract 1
- MZVQICATKBPMCP-UHFFFAOYSA-N C(CC1=C(SC=C1)NC(=O)OCC)C1=C(SC=C1)NC(=O)OCC Chemical compound C(CC1=C(SC=C1)NC(=O)OCC)C1=C(SC=C1)NC(=O)OCC MZVQICATKBPMCP-UHFFFAOYSA-N 0.000 abstract 1
- LYFLZRMWNFHOOJ-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCC)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C Chemical compound C(CCCCCCCCCCCCCCCC)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C LYFLZRMWNFHOOJ-UHFFFAOYSA-N 0.000 abstract 1
- DVVXYXYZYBFSCM-UHFFFAOYSA-L C1(=CC(=CC=C1)C1=C(SC=C1C1=CC=CC=C1)NC(=O)[O-])C1=C(SC=C1C1=CC=CC=C1)NC(=O)[O-] Chemical compound C1(=CC(=CC=C1)C1=C(SC=C1C1=CC=CC=C1)NC(=O)[O-])C1=C(SC=C1C1=CC=CC=C1)NC(=O)[O-] DVVXYXYZYBFSCM-UHFFFAOYSA-L 0.000 abstract 1
- YXNQOAGWFSXNPE-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C Chemical compound C1(=CC=CC=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C YXNQOAGWFSXNPE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N Hexamethylenediamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 abstract 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 1
- SCZVXVGZMZRGRU-UHFFFAOYSA-N N'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 abstract 1
- XFRRCZKVZVLCRW-UHFFFAOYSA-N S(=O)(=O)(O)C1=CC=C(C=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C Chemical compound S(=O)(=O)(O)C1=CC=C(C=C1)C1=C(SC=C1)NC(=O)OC1=CC=C(C=C1)C XFRRCZKVZVLCRW-UHFFFAOYSA-N 0.000 abstract 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 229910052751 metal Chemical class 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 229950000244 sulfanilic acid Drugs 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Thiolcarbamic esters are manufactured by bringing into interaction an S-ester of thiolchloroformic acid, of the formula R(SCOC1)m, and a primary amine R1(NH2)n (or a salt thereof), wherein R and R1 represent hydrocarbon radicals, substituted or unsubstituted, the same or different, m is 1 or 2 and n is 1, 2, 3, 4 or 5, in the presence of an acid-binding agent which does not react with an S-ester of thiolchloroformic acid under the conditions of the reaction, e.g. an inorganic acid-binding agent such as sodium hydroxide or an organic acid-binding agent such as a tertiary amine or a metal salt of an organic acid. The reaction is preferably carried out at 0-10 DEG C., and conveniently in the presence of a solvent, which, when the primary amine is used in the form of a water-soluble salt, is preferably water. In examples: (1) p-tolyl thiolchloroformate is stirred with heptadecylamine in ethyl alcohol in the presence of dimethylaniline to produce p-tolyl heptadecylthiolcarbamate; the heptadecylamine may be replaced by p-aminophenol, m-phenylenediamine or a -naphthylamine; (2) ethylenediamine similarly (but using benzene as solvent) yields di-p-tolyl ethylene-bis-(thiolcarbamate); the ethylenediamine may be replaced by hexamethylene diamine, 1 : 3 : 5-triamino-2 : 4 : 6-triethylbenzene or aniline; (3) a -naphthylamine is treated as in (1), except that sodium acetate or sodium hydroxide is used as the acid-binding agent, producing p-tolyl a -naphthylthiolcarbamate; (4) aqueous sulphanilic acid similarly (using sodium hydroxide) gives p-tolyl p-sulphophenylthiolcarbamate; (5) p-aminobenzoic acid or b -alanine is treated as in (4) to produce p-tolyl p-carboxyphenyl- or b -carboxyethyl-thiolcarbamate; (6) ethyl thiolchloroformate and ethylenediamine are reacted as in (1) to form diethyl ethylene-bis-(thiolcarbamate); (7) p-tolyl thiolchloroformate is stirred with aniline in ethyl alcohol in the presence of triethylamine to yield p-tolyl phenylthiolcarbamate; (8) the ethyl alcohol and triethylamine in (7) are replaced by petroleum ether and pyridine; (9) m-phenylene-bis-(thiolchloroformate) is stirred with aniline in benzene in the presence of dimethylaniline to form m-phenylene-bis-(phenylthiolcarbamate); (10) 4 : 41 : 411-triaminotriphenylmethane trihydrochloride is stirred with p-tolyl thiolchloroformate in aqueous solution in the presence of dimethylaniline to give tri-p-tolyl triphenylmethane-4 : 41 : 411-tris-(thiolcarbamate); the triaminotriphenylmethanetrihydrochloride may be replaced by 2 : 4 : 31-triaminostilbene trihydrochloride, 2 : 4 : 21 : 41-tetraminostilbene tetrahydrochloride or 2 : 4 : 21 : 41 : 311-pent amino-5 : 51-dimethyltriphenylmethane pentahydrochloride; (11) ethyl thiolchloroformate is treated as in the first part of (10) to produce triethyl triphenylmethane - 4 : 41 : 411 - tris - (thiolcarbamate). Additional amines specified are ethyl p-aminobenzoate and 1 : 5-pentanolamine. 1 : 3 : 5-Triamino-2 : 4 : 6-triethylbenzene is obtainable by hydrogenating 1 : 3 : 5-trinitro-2 : 4 : 6-triethylbenzene.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599179A true GB599179A (en) | 1948-03-05 |
Family
ID=1739423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2568545A Expired GB599179A (en) | 1945-10-03 | Thiolcarbamic esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599179A (en) |
Cited By (5)
| 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 |
| DE1300947B (en) * | 1961-05-01 | 1969-08-14 | Stauffer Chemical Co | Alkyl l-hexamethyleneiminocarbothiolate |
| FR2189386A1 (en) * | 1972-05-26 | 1974-01-25 | Stauffer Chemical Co |
-
1945
- 1945-10-03 GB GB2568545A patent/GB599179A/en not_active Expired
Cited By (6)
| 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 |
| DE1300947B (en) * | 1961-05-01 | 1969-08-14 | Stauffer Chemical Co | Alkyl l-hexamethyleneiminocarbothiolate |
| FR2189386A1 (en) * | 1972-05-26 | 1974-01-25 | Stauffer Chemical Co | |
| US3846466A (en) * | 1972-05-26 | 1974-11-05 | Stauffer Chemical Co | Esters of di-(thiocarbamoyl)ethylene as juvenile hormone mimicking agents for control of insects |
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