1-(Bromomethyl)-2,4-difluorobenzene → N-benzenesulfonyl-4-acetylamino-3-(2,4-difluorobenzylamino)benzamide

HRID 276025Notes

Reaction equation

HRID 276025 reaction equation
[C:1]1([S:7]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([NH2:22])[CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:26]=1[CH2:27]Br.C(=O)([O-])O.[K+]>CO>[C:1]1([S:7]([NH:10][C:11](=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([NH:22][CH2:27][C:26]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:25]=3[F:24])[CH:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 516893Potassium BicarbonateHCID 18680999N-benzenesulfonyl-4-acetylamino-3-aminobenzamide

Product 1

HCID 18680987N-benzenesulfonyl-4-acetylamino-3-(2,4-difluorobenzylamino)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7 ml of methanol containing 0.60 g of N-benzenesulfonyl-4-acetylamino-3-aminobenzamide, 0.656 g of 2,4-difluorobenzyl bromide and 0.423 g of potassium hydrogencarbonate was stirred at 60° C. for 1 hour. The reaction solution was concentrated, and the residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1) to give 0.370 g of N-benzenesulfonyl-4-acetylamino-3-(2,4-difluorobenzylamino)benzamide.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified through silica-gel column chromatography (eluent
  3. additiona mixture of ethyl acetate and methanol at a ratio of 9:1)

Sources & evidence

ORD record
ord-41ebf3841b5b42cdbc681cf9b200f403
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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