Methanethiol → HCID 86758599, compound

HRID 1017814Notes

Reaction equation

HRID 1017814 reaction equation
C(N(CC)CC)C.[CH3:8][SH:9].[CH3:10][O:11][C:12](=[O:44])[C:13](=[N:32]OS(C1C=CC(C)=CC=1)(=O)=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([O:28][N:29]=[CH:30][CH3:31])[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[CH3:10][O:11][C:12](=[O:44])[C:13](=[N:32][S:9][CH3:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([O:28][N:29]=[CH:30][CH3:31])[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 8471TriethylamineHCID 86758600HCID 86758600, compound

Product 1

HCID 86758599HCID 86758599, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2 ml triethylamine in 15 ml chloroform saturated with methanethiol are added 5.15 g (10 mmol) 2-{2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-phenyl}-tosyloxyimino-acetic acid methyl ester. The mixture was stirred at room temperature for 48 hours. After evaporation the residue is purified by silicagel chromatography (ethyl acetate 1, hexanes 5) to give—after elution of 2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-benzonitrile as by-product—1.0 g (28%) of the 2-{2-[1-(4-chloro-phenyl)-ethylideneamino-oxymethyl]-phenyl}-methylthioimino-acetic acid methyl ester. Melting point of 112-113° C.

Workup

  1. customAfter evaporation the residue
  2. customis purified by silicagel chromatography (ethyl acetate 1, hexanes 5) to
  3. washgive—after elution of 2-[1-(4-chloro-phenyl)-ethylideneaminooxymethyl]-benzonitrile as by-product—1.0 g (28%) of the 2-{2-[1-(4-chloro-phenyl)-ethylideneamino-oxymethyl]-phenyl}-methylthioimino-acetic acid methyl ester

Sources & evidence

ORD record
ord-5b2febc59a214ae8b9f23d3a494cc3e8
Source dataset
uspto-grants-2002_11
Patent number
US06479550B1

Reaction notes

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