Sulfuryl chloride → 2-Methyl-1-benzothiophene-3-sulfonyl chloride
Reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH:8]=1>CN(C)C=O>[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[S:1]([Cl:5])(=[O:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Sulfuryl chloride (9.5 mmoles, 0.76 ml) was added to a stirred solution of dimethylformamide (DMF; 11.2 mmoles, 0.87 ml) at 0° C., and the resulting faint yellow solution was stirred for 20 min at 0° C. 2-Methylbenzo[b]thiophene (5.6 mmoles, 0.83 g) was then added, the reaction mixture was diluted with 2 ml of DMF, and then heated to 85° C. After 2.5 hrs at 85° C., the brown reaction mixture was cooled to ambient temperature and added to ice (100 ml). The aqueous phase was extracted with ethyl acetate (100 ml), and the organic phase was dried (MgSO4), filtered and concentrated to collect an orange-brown solid. Flash chromatography (4% ethyl acetate/hexanes) provided 0.89 g (640%) of 2-methylbenzo[b]thiophene-3-sulfonyl chloride as a yellow solid.
Workup
- temperatureheated to 85° C
- waitAfter 2.5 hrs at 85° C.
- temperaturethe brown reaction mixture was cooled to ambient temperature
- extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
- dry with materialthe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customto collect an orange-brown solid
Sources & evidence
- ORD record
- ord-26959f2714b345f7ac1c6b0d4f63cc8c
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06331637B1
Reaction notes
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