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

HRID 591147Notes

Reaction equation

HRID 591147 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].[Br:19]N1C(=O)CCC1=O.O>ClCCl.C(#N)C>[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[Br:19])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

Product 1

HCID 72549384N-(3-bromo-2-butyl-5-benzofuranyl)MethanesulfonamideYield 71%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

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 5.34 g (0.03 mol, 1.5 eq) of N-bromosuccinimide in 60 mL of acetonitrile is added dropwise at −8±2° C. in 30 min. The reaction mixture is stirred for 3 hours at this temperature and then is poured into 150 mL of water. The product is extracted with 2×60 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 4.89 g (71%) of the title compound (IIIb) as an orange solid.

Workup

  1. extractionThe product is extracted with 2×60 mL of dichloromethane
  2. customThe organic layer is evaporated
  3. customthe residue is purified by column chromatography (spheric silica; eluent: toluene:methanol=7:3)

Sources & evidence

ORD record
ord-5e253a28db854d95959421a0b65e7f42
Source dataset
uspto-grants-2016_01
Patent number
US09238636B2

Reaction notes

Loading…