Dimethylformamide → 2-[3,4-(Methylenedioxy)benzyl]-benzo[b]thiophene-3-sulfonylchloride

HRID 2270621Notes

Reaction equation

CN(C=O)C.[S:6]([Cl:10])(Cl)(=[O:8])=[O:7].[CH2:11]1[O:29][C:28]2[CH:27]=[CH:26][C:15]([CH2:16][C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[CH:18]=3)=[CH:14][C:13]=2[O:12]1>>[CH2:11]1[O:29][C:28]2[CH:27]=[CH:26][C:15]([CH2:16][C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[S:6]([Cl:10])(=[O:8])=[O:7])=[CH:14][C:13]=2[O:12]1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24648Sulfuryl chloride

HCID 229984072-[3,4-(Methylenedioxy)benzyl]benzo[b]thiophene

Product 1

HCID 229983852-[3,4-(Methylenedioxy)benzyl]-benzo[b]thiophene-3-sulfonylchloride

Procedure

2-[3,4-(methylenedioxy)benzyl]benzo[b]thiophene-3-sulfonyl chloride was prepared by the method of Example 40B using DMF (9.1 mmoles, 0.70 ml), sulfuryl chloride (7.7 mmoles, 0.62 ml) and 2-[3,4-(methylenedioxy)benzyl]benzo[b]thiophene (4.6 mmoles, 1.2 g). Flash chromatography (5% ethyl acetate/hexanes) provided 0.71 g (42%) of a light yellow solid.

Sources & evidence

ORD record: ord-3a05de80c1a2424a991361b9b00b8d87
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331637B1

Reaction notes

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