Dimethylformamide → 2-Ethyl-5-methylbenzo[b]thiophene-3-sulfonylchloride

HRID 1166903Notes

Reaction equation

CN(C=O)C.[S:6]([Cl:10])(Cl)(=[O:8])=[O:7].[CH2:11]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=2[CH:14]=1)[CH3:12]>>[CH2:11]([C:13]1[S:17][C:16]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=2[C:14]=1[S:6]([Cl:10])(=[O:8])=[O:7])[CH3:12]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24648Sulfuryl chloride

HCID 5953442-Ethyl-5-methylbenzo[b]thiophene

Product 1

HCID 229984372-Ethyl-5-methylbenzo[b]thiophene-3-sulfonylchloride

Procedure

2-ethyl-5-methylbenzo[b]thiophene-3-sulfonylchloride was prepared in the same manner as described in Example 40B. Reaction of DMF (6.5 mmoles, 0.50 ml), sulfurylchloride (5.5 mmoles, 0.44 ml) and 2-ethyl-5-methylbenzo[b]thiophene (3.2 mmoles, 0.57 g) yielded, after flash chromatography, using 2% ethyl acetate/hexanes, 0.58 g (66%) of an orange solid.

Workup

customyielded

Sources & evidence

ORD record: ord-37b90b7045074b1485a4529e85cb04fa
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613804B2

Reaction notes

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