Hydrochloric Acid → 1-Benzofuran-2-Sulfonamide
Reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Li]CCCC.[S:15](Cl)(Cl)(=[O:17])=[O:16].[NH4+:20].[OH-].Cl>C1COCC1.CCCCCC.CC(C)=O.O>[O:1]1[C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[C:5]1[S:15]([NH2:20])(=[O:17])=[O:16]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of benzo[b]furane (2.5 mmol) in dry THF (1.5 mL) and cooled to 0° C. is slowly added 1.6 M n-BuLi in hexane (1.7 mL, 2.5 mmol). The temperature is maintained at 0° C. and the reaction mixture is stirred for 20 min. Then the heterogeneous mixture is diluted with 2 mL of THF and is transferred by canula to a well-stirred solution of sulfuryl chloride (410 μL, 5.1 mmol) in hexane (2.0 mL) at 0° C. After 1 hr, the suspension is diluted with acetone and the resulting solution of the corresponding sulfonyl chloride is added slowly to a solution of 2 mL of NH4OH in acetone (5 mL). The mixture is diluted with water and acidified with concentrated HCl and the product extracted into ethyl acetate. The organic phase is washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel chromatography (eluent: hexane 4/ethyl acetate 1) to afford the title compound (211 mg, 43%).
Workup
- waitAfter 1 hr
- extractionthe product extracted into ethyl acetate
- washThe organic phase is washed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe crude product is purified by silica gel chromatography (eluent: hexane 4/ethyl acetate 1)
Sources & evidence
- ORD record
- ord-4853e0436500404d995d8ecfa3d3b30d
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282595B2
Reaction notes
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