Thionyl Chloride → [(Diphenylmethyl)sulfanyl]acetyl chloride

HRID 457254Notes

Reaction equation

[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8][CH2:9][C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:21])=O>>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8][CH2:9][C:10]([Cl:21])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 20778862-Benzhydrylsulfanylacetic acid

Product 1

HCID 14181405[(Diphenylmethyl)sulfanyl]acetyl chloride

Procedure

2-[(Diphenylmethyl)thio]acetic acid (III), on reaction with thionyl chloride yielded the corresponding 2-[(diphenylmethyl)thio]acetylchloride (IV), which on reaction with ammonia produced 2-[(diphenylmethyl)thio]acetamide (I) which on oxidation with hydrogen peroxide resulted in modafinil (II).

Sources & evidence

ORD record: ord-c5991789c2934795ba36bdaabc72d005
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186860B2

Reaction notes

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