Thionyl Chloride → 2-Acetylthiomethyl-3-phenyl-propionyl chloride

Reaction equation

[C:1]([S:4][CH2:5][C@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7](O)=[O:8])(=[O:3])[CH3:2].S(Cl)([Cl:19])=O>>[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([Cl:19])=[O:8])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 7019602(R)-2-acetylthiomethyl-3-phenylpropanoic acid

Product 1

HCID 103777342-Acetylthiomethyl-3-phenyl-propionyl chloride

Procedure

2.0 g (8.40 mmol) of (R)-2-acetylthiomethyl-3-phenylpropanoic acid (Ia R) (Example 1, stage e) are placed in a round-bottomed flask. The flask is cooled by an ice-water bath and 1.2 g (10.08 mmol) of thionyl chloride are added dropwise. The mixture is stirred overnight to room temperature.

Workup

temperatureThe flask is cooled by an ice-water bath

Sources & evidence

ORD record: ord-09377bdea0a4475086783cea02161020
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013829

Reaction notes

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