Thionyl Chloride → HCID 54397907, compound

HRID 864748Notes

Reaction equation

[CH:1]([C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([CH3:3])[CH3:2].S(Cl)([Cl:16])=O>>[CH:1]([C:4]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:5]=1[C:6]([Cl:16])=[O:7])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 221014761339564-41-8

Product 1

HCID 54397907HCID 54397907, compound

Procedure

Reaction of 2-isopropyl-4-fluorobenzoic acid with thionyl chloride affords 2-isopropyl-4-fluorobenzoyl-chloride, which, on reaction with diethylamine, affords 2-isopropyl-4-fluoro-N,N-diethylbenzamide. Reaction of the latter with s-butyl lithium and reaction of the resulting lithium salt with sulfur dioxide followed by sodium hydroxylamine-O-sulfonate affords 2-isopropyl-4-fluoro-6-aminosulfonyl-N,N-diethylbenzamide, which, on heating in glacial acetic acid, affords 4-isopropyl-6-fluorosaccharin.

Sources & evidence

ORD record: ord-4e8310ecf88c4d3ab28b840798279335
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563163

Reaction notes

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