Water → N-[4-(benzenesulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

HRID 327163Notes

Reaction equation

HRID 327163 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[C:15]1([S:21]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C(=O)C>[C:15]1([S:21]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:28][CH:29]=2)(=[O:22])=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 5166664-(Phenylsulfonyl)anilineHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Product 1

HCID 5240098N-[4-(benzenesulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (3.96 g 25 mmol) in N,N-dimethylacetamide (36 mL) was rapidly added thionyl chloride (3.10 g, 26 mmol) and the mixture (a precipitate formed after a few minutes) stirred at -15° C. to -5° C. for 1 hour. 4-(Phenylsulfonyl)benzenamine (3.97 g, 17 mmol) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into water, the resulting solid was filtered off, washed with 3N HCl, then water and dried at 65° C. for 2 hours. The solid was dissolved in 300 mL of refluxing methylene chloride and stirred and heated as hexane was added to replace the methylene chloride as it boiled off. When 250 mL of hexane had been added (precipitate formed at about 180 mL addition) the mixture was concentrated to 250 mL and refrigerated. The yield of light tan solid was 5.92 g (93%), mp 164°-166° C. 1H--NMR (250 MHz, d6 --DMSO): 1.59 (s, 3H, CH3), 7.57-7.72 (m, 4H, OH, aromatic), 7.92-8.04 (m, 6H, aromatic), 10.43 (s, 1H, NH).

Workup

  1. customthe mixture (a precipitate formed after a few minutes)
  2. stirringto stir at room temperature overnight
  3. filtrationthe resulting solid was filtered off
  4. washwashed with 3N HCl
  5. dry with materialwater and dried at 65° C. for 2 hours
  6. dissolutionThe solid was dissolved in 300 mL of refluxing methylene chloride
  7. stirringstirred
  8. temperatureheated as hexane
  9. additionwas added
  10. additionWhen 250 mL of hexane had been added
  11. custom(precipitate formed at about 180 mL addition) the mixture
  12. concentrationwas concentrated to 250 mL

Sources & evidence

ORD record
ord-cdd46bad76d54d5db8c46be330c96c5e
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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