Methanethiol → HCID 15340168, compound

HRID 266412Notes

Reaction equation

HRID 266412 reaction equation
[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].CS.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].[CH2:22]([SH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([S:29][C:12]1[C:13]([N+:19]([O-:21])=[O:20])=[CH:14][CH:15]=[CH:16][C:17]=1[Cl:18])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 878MethanethiolHCID 7509Benzyl mercaptanHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 185552,3-Dichloronitrobenzene

Product 1

HCID 15340168HCID 15340168, compoundYield 56%

Procedure

It is known to convert chloronitrobenzenes containing activated chlorine atoms to the corresponding aryl methyl sulphides in alcoholic solution or suspension, in the presence of sodium hydroxide solution or potassium carbonate, by the introduction of methanethiol (Houben-Weyl, vol. E 11 (1985), p. 175). The yields achieved by this method, however, are only 52-78% of theory. The reaction of 2,3-dichloro-nitrobenzene with benzylmercaptan in the presence of a base gave 2-chloro-6-nitrophenyl benzyl sulphide in only 56% yield (Bull. 1951, 621-626).

Sources & evidence

ORD record
ord-686f466795fc482c8a246375613fc247
Source dataset
uspto-grants-1997_07
Patent number
US05650542

Reaction notes

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