Thionyl Chloride → HCID 10970229, compound

HRID 991882Notes

Reaction equation

HRID 991882 reaction equation
[C:1]1([S:7]([O:10][C:11]2[CH:22]=[CH:21][C:14]3[S:15][CH:16]=[C:17]([C:18](O)=[O:19])[C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:25])=O>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]1([S:7]([O:10][C:11]2[CH:22]=[CH:21][C:14]3[S:15][CH:16]=[C:17]([C:18]([Cl:25])=[O:19])[C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 9862505HCID 9862505, compound

Product 1

HCID 10970229HCID 10970229, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

The 5-benzenesulfonyloxybenzo[b]thiophene-3-carboxylic acid (12) (5.582 g, 16.7 mmol) prepared above was refluxed with dimethylformamide (1 drop), thionyl chloride (3.57 ml, 50 mmol) and toluene (22 ml) for 1.5 hours. When the solvent was removed under reduced pressure, 5.89 g of the objective compound (6) was obtained.

Workup

  1. customWhen the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f7cf232dabda453f8d773765ce88959a
Source dataset
uspto-grants-2002_10
Patent number
US06465662B1

Reaction notes

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