Benzenesulfenyl chloride → 2-Phenylthio-5-(3,4-xylyl)thiophene

HRID 46649

Reaction equation

HRID 46649 reaction equation
[C:1]1([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=1.[C:14]1([S:20]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Fe].C(Cl)(Cl)(Cl)Cl>[C:14]1([S:20][C:11]2[S:10][C:9]([C:1]3[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=3)=[CH:13][CH:12]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 11008040Benzenesulfenyl chlorideHCID 199050092-(3,4-Xylyl)thiophene2×

Product 1

HCID 203866552-Phenylthio-5-(3,4-xylyl)thiopheneYield 29.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 37 g (0.197 mole) of 2-(3,4-xylyl)thiophene, 200 ml of reagent carbon tetrachloride, 29 ml (36 g, 0.259 mole) of benzenesulfenyl chloride and 0.05 g of iron powder was allowed to stand two days at room temperature. A vapor phase chromatogram of the mixture showed that all the 2-(3,4-xylyl)thiophene had been consumed. The carbon tetrachloride was removed by distillation and the residue recrystallized from ethanol to give a first crop of 17 g (29%) of 2-phenylthio-5-(3,4-xylyl)thiophene, m.p. 77°-78° C.

Workup

  1. customhad been consumed
  2. customThe carbon tetrachloride was removed by distillation
  3. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-f4ee1ab59c0149929c9669971a4cb76b
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Linked notes

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