GB814213A - Cyano substituted aliphatic isothiocyanates - Google Patents
Cyano substituted aliphatic isothiocyanatesInfo
- Publication number
- GB814213A GB814213A GB3149356A GB3149356A GB814213A GB 814213 A GB814213 A GB 814213A GB 3149356 A GB3149356 A GB 3149356A GB 3149356 A GB3149356 A GB 3149356A GB 814213 A GB814213 A GB 814213A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyanoalkyldithiocarbamate
- mol
- equivalent
- preparation
- inert
- 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 aliphatic isothiocyanates Chemical class 0.000 title abstract 10
- 125000004093 cyano group Chemical group *C#N 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- GKSHESNLYRAIJS-UHFFFAOYSA-N 15-isothiocyanatopentadecanenitrile Chemical class S=C=NCCCCCCCCCCCCCCC#N GKSHESNLYRAIJS-UHFFFAOYSA-N 0.000 abstract 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula NC(A)N = C = S wherein A represents an alkylene radical having from 2-14 carbon atoms, the chain being either straight or branched, and the preparation thereof wherein (A) a cyanoalkamine is reacted with carbon disulphide in the presence of a tertiary amine, preferably triethyamine, and in an inert solvent, preferably an inert chlorinated solvent such as chloroform, to form the corresponding cyanoalkyldithiocarbamate salt, ethyl chloroformate is added to form the carbethoxy cyanoalkyldithiocarbamate which is decomposed by the addition of one mol. equivalent of a tertiary base to give a cyanoalkylisothiocyanate; or (B) a cyanoalkamine is reacted with carbon disulphide in the presence of a tertiary amine such as triethylamine, and in an inert solvent, preferably an inert chlorinated solvent such as methylene chloride, to form the cyanoalkyldithiocarbamate salt which is oxidized with sodium hypochlorite to form the cyanoalkylisothiocyanate. Examples are given of the preparation of the following compounds either by method (A) or (B) or both: 2-cyanoethyl-, 1-methyl-2-cyanoethyl -, 2 - cyanopropyl -, 3 - cyanopropyl -, 4 - cyanobutyl -, 5 - cyanopentyl -, 6-cyanohexyl -, 10 - cyanodecyl -, and 14 - cyanotetradecylisothiocyanates. The Provisional Specification relates to compounds of the general formula CN(CH2)nN = C = S, in which n is an integer from 2 to 18 and the preparation thereof by treating the aminonitrile in aqueous solution at a temperature between 0 DEG and 20 DEG C. in the presence of one mol. equivalent of a base, for example ammonium, potassium or sodium hydroxide or triethylamine, with one mol. equivalent of carbon disulphide. No additional examples are given.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US689758A US2886584A (en) | 1956-10-16 | 1957-10-14 | Cyano substituted aliphatic isothiocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814213A true GB814213A (en) | 1959-06-03 |
Family
ID=1742581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3149356A Expired GB814213A (en) | 1956-10-16 | 1956-10-16 | Cyano substituted aliphatic isothiocyanates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB814213A (en) |
-
1956
- 1956-10-16 GB GB3149356A patent/GB814213A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB891600A (en) | New tertiary amine salts and a method of setting hair with them | |
| GB814213A (en) | Cyano substituted aliphatic isothiocyanates | |
| GB1435585A (en) | S-triazinediones and their use as herbicides | |
| KR840000493A (en) | Method for preparing herbicide comprising amide and ester group derived from pyridine | |
| KR940014366A (en) | Method for preparing 2-iminothiazoline derivatives and intermediates thereof | |
| GB1119696A (en) | Process for the preparation of thiuram monosulphides | |
| ES420697A1 (en) | Chlorinated mandelamidines | |
| GB948783A (en) | New thiophosphoric acid ester derivatives having insecticidal properties | |
| GB1000194A (en) | Aziridine compounds and method of preparing same | |
| GB1047061A (en) | Polymers and a process for the preparation thereof | |
| GB1008260A (en) | Process for the production of substituted benzofuran derivatives | |
| GB961678A (en) | Process for the manufacture of thiuram disulphides | |
| ATE8875T1 (en) | PROCESS FOR CONTINUOUS PRODUCTION OF DICHLORACETAMIDES. | |
| GB921536A (en) | Substituted n-hydroxyureas and a process for their manufacture | |
| GB1473289A (en) | Process for the alpha-chlorination of alkyl chloroaromatic compounds | |
| GB887701A (en) | Processes for the preparation of benzo-1:3-thiazinediones-(2:4) | |
| KR860007245A (en) | Process for preparing piperazinylmethyl-1,2,4-triazolylmethyl-carbinol | |
| US3285770A (en) | Process for the treatment of cellulose textile materials with hardenable resin precondensation products and brightening agents | |
| GB977479A (en) | New and useful organopolysiloxanes and use thereof | |
| ES273768A1 (en) | Method of killing nematodes with compositions comprising dithiocarbamic acid derivatives | |
| CS231985B1 (en) | Manufacturing process of hydrocarbon solution of alkylsodium compound | |
| GB948522A (en) | Pyrazinylphosphoroamidothioates and method for preparing the same | |
| GB1000210A (en) | Polymers from diisocyanates | |
| RO85314A (en) | PROCESS FOR PREPARING PYRIDYLPROPYLTIOCARBONATES | |
| GB1098598A (en) | Substituted n-tertiary-aminoalkyl-benzamides and their preparation |