Water → N-(2-butyl-3-chloro-5-benzofuranyl)Methanesulfonamide

HRID 591146Notes

Reaction equation

[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].C(#N)C.[Cl:22]N1C(=O)CCC1=O.O>ClCCl>[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])=[CH:10][C:8]=2[C:9]=1[Cl:22])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

5.34 g (0.02 mol) of N-(2-butyl-1-benzofuran-5-yl)methanesulfonamide (II) is dissolved in 60 mL of dichloromethane and 60 mL of acetonitrile is added to the solution. 5.34 g (0.04 mol, 2 eq) of N-chlorosuccinimide in solid form is added dropwise at −8±2° C. in 20 min. The reaction mixture is stirred for 2 hours at this temperature and then heated up to 20° C. The reaction mixture is poured into 200 mL of water. The product is extracted with 2×80 mL of dichloromethane. The organic layer is evaporated and the residue is purified by column chromatography (spheric silica; eluent: toluene:methanol=7:3) to give 4.59 g (76%) of the title compound (IIIa) as a yellowish-brown solid.

Workup

extractionThe product is extracted with 2×80 mL of dichloromethane
customThe organic layer is evaporated
customthe residue is purified by column chromatography (spheric silica; eluent: toluene:methanol=7:3)

Sources & evidence

ORD record: ord-ab3d102f3d6148ceafc2184deae8e3c2
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238636B2

Reaction notes

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