Thionyl Chloride → HCID 10970229, compound

HRID 2185138Notes

Reaction equation

HRID 2185138 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-5c66a00614fa4c2a8433db40a7217d79
Source dataset
uspto-grants-2002_06
Patent number
US06399788B1

Reaction notes

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