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 (64%) 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-95497283c0c64e99a0681a28377dcecd
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962490
Reaction notes
Loading…