Water → 3'-(2-Dibenzylaminoacetyl)-4'-fluoromethanesulfonanilide

HRID 2379184Notes

Reaction equation

HRID 2379184 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[F:16])[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[O:4].[CH2:17]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:25]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[F:16])[NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[O:4])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7656DibenzylamineHCID 221413933'-(2-Bromoacetyl)-4'-fluoromethanesulfonanilide

Product 1

HCID 189580893'-(2-Dibenzylaminoacetyl)-4'-fluoromethanesulfonanilideYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3'-(2-Bromoacetyl)-4'-fluoromethanesulfonanilide (30 g) was dissolved in 200 ml of N,N-dimethylformamide, a solution of 38 g of dibenzylamine in N,N-dimethylformamide was added with ice-cooling and stirring and the mixture was made to react at room temperature for 1 hour. The reaction mixture was added to water followed by extracting with ethyl acetate. The extract was washed with water, dried, the solvent was evaporated therefrom and the residue was crystallized from diisopropyl ether to give 35 g of 3'-(2-dibenzylaminoacetyl)-4'-fluoromethanesulfonanilide. The crystals were made into hydrochloride to give 35 g of crystals, m.p. 185°-188° C.

Workup

  1. temperaturecooling
  2. customto react at room temperature for 1 hour
  3. extractionby extracting with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5a963038e9db42a18b8ec211a5c078ab
Source dataset
uspto-grants-1994_11
Patent number
US05360822

Reaction notes

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