Thionyl Chloride → Benzylthiocarbonyl chloride

HRID 635016

Reaction equation

[C:1]1([CH2:7][C:8](O)=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:13])=O>>[C:1]1([CH2:7][C:8]([Cl:13])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 178526157HCID 178526157, compound

Product 1

HCID 19906501Benzylthiocarbonyl chlorideYield 92%

Conditions

Temperature: 40 °C

Procedure

A quantity of 762 g (4.536 mol) of 2-phenylthioacetic acid is stirred at room temperature for 3 hours with thionyl chloride (375 ml, 5.14 mol), then stirred at 40° C. for 3 hours. Rotary evaporation followed by bulb-to-bulb distillation gives 777 g (4.166 mol, 92%) of 2-phenylthioacetyl chloride.

Workup

customRotary evaporation
distillationfollowed by bulb-to-bulb distillation

Sources & evidence

ORD record: ord-0760fb33a1f3464893b600b1f5082067
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184540B2

Linked notes

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