Methyl Thioglycolate → 3-(2'-Chloro-4'-trifluoromethylphenoxy)-6-nitrophenyl methoxycarbonylmethyl disulfide

HRID 485618Notes

Reaction equation

HRID 485618 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[Cl:7][C:8]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:9]=1[O:10][C:11]1[CH:12]=[C:13]([S:20]Cl)[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1>CCOCC>[CH3:6][O:5][C:1]([CH2:2][S:3][S:20][C:13]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=[C:11]([O:10][C:9]2[CH:22]=[CH:23][C:24]([C:26]([F:27])([F:28])[F:29])=[CH:25][C:8]=2[Cl:7])[CH:12]=1)=[O:4]

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 13246608HCID 13246608, compound

Product 1

HCID 132466093-(2'-Chloro-4'-trifluoromethylphenoxy)-6-nitrophenyl methoxycarbonylmethyl disulfideYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5.3 parts by weight of methyl thioglycolate were added dropwise to a solution of 19.2 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrobenzenesulfenyl chloride in 100 parts by volume of absolute ether at room temperature, the reaction mixture was stirred for a further two hours and then evaporated to dryness under reduced pressure, and the oily residue was crystallized using diisopropyl ether. 25 parts by weight (90% yield) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrophenyl methoxycarbonylmethyl disulfide of melting point 66°-68° C. were obtained (compound No. 3).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customthe oily residue was crystallized

Sources & evidence

ORD record
ord-cd672482ced44571bc5ae432dc9152df
Source dataset
uspto-grants-1985_08
Patent number
US04537621

Reaction notes

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