Thionyl Chloride → 4-(Trichloromethyl)benzoyl chloride

HRID 864744Notes

Reaction equation

HRID 864744 reaction equation
[Cl:1][C:2]([Cl:13])([Cl:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>>[Cl:1][C:2]([Cl:13])([Cl:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2870154-(Trichloromethyl)benzoic acid

Product 1

HCID 846604-(Trichloromethyl)benzoyl chloride

Procedure

Reaction of 4-trichloromethylbenzoic acid with thionyl chloride affords 4-trichloromethylbenzoyl chloride, which, on reaction with diethylamine, affords 4-trichloro-methyl-N,N-diethylbenzamide. Following a procedure similar to that described in Preparation 5, reaction of the latter with s-butyl 10 lithium and reaction of the resulting lithium salt with sulfur dioxide followed by sodium hydroxylamine-O-sulfonate affords 4-trichloromethyl-2-aminosulfonyl-N,N-diethylbenzamide, which, on heating in glacial acetic acid, affords 6-trichloromethylsaccharin.

Sources & evidence

ORD record
ord-a796b55e536a47d882ff234c3dbd8bdf
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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