Triethylamine → Benzamide, 3-[(2,4-difluorophenyl)thio]-4-[(methylsulfonyl)amino]-

HRID 1087213Notes

Reaction equation

HRID 1087213 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>ClCCl>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[S:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10016498HCID 10016498, compound

Product 1

HCID 10361027Benzamide, 3-[(2,4-difluorophenyl)thio]-4-[(methylsulfonyl)amino]-Yield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-3-(2,4-difluorophenylthio)benzamide (0.82 g), methanesulfonyl chloride (0.64 g) and triethylamine (0.6 g) in dichloromethane (10 ml) was stirred for 2 hours at room temperature. The reaction mixture was evaporated. To the residue were added methanol (10 ml) and potassium hydroxide (0.6 g). The mixture was kept overnight and evporated. The residue was treated with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue obtained was recrystallized from ethanol to give 3-(2,4-difluorophenylthio)-4-(methanesulfonamido)benzamide (0.54 g).

Workup

  1. customThe reaction mixture was evaporated
  2. additionTo the residue were added methanol (10 ml) and potassium hydroxide (0.6 g)
  3. waitThe mixture was kept overnight
  4. additionThe residue was treated with diluted hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-10cedef23d76446095ec18da97cdee7d
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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