Water → HCID 10787580, compound

HRID 2259666Notes

Reaction equation

HRID 2259666 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.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23].O>CN(C)C(=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:27][CH:26]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 459381HCID 459381, compoundHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Product 1

HCID 10787580HCID 10787580, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.89 g, 5.6 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.67 g, 5.6 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-(2-Chlorophenylsulfonyl)benzenamine (1.00 g, 3.7 mmol) was added in one portion to the orange solution and the mixture stirred at room temperature overnight. The brown solution was poured into water and the aqueous solution extracted with ethyl acetate (2×50 mL). The organics were combined, washed with water, dried (MgSO4), filtered and the solvent distilled to yield a tan solid. Recrystallization from methylene chloride/hexane yielded the title propanamide (1.43 g, 94%) as an off-white solid; mp 136°-138° C. 1H-NMR (250 MHz, d6 -DMSO): 1.58 (s, 3H, CH3), 7.57 (s, 1H, OH), 7.67 (m, 3H, aromatic), 7.88 (d, 2H, J=8.8 Hz, aromatic), 8.02 (d, 2H, J=8.8 Hz, aromatic), 8.26 (d, 1H, J=6.6 Hz, aromatic), 10.46 (s, 1H, NH). MS (CI, CH4): 408(M+1). Analysis for C16H13ClF3NO4S: Calculated: C, 47.13; H, 3.22; N, 3.43 Found: C, 46.93; H, 3.17; N, 3.40

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. extractionthe aqueous solution extracted with ethyl acetate (2×50 mL)
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. distillationthe solvent distilled
  7. customto yield a tan solid
  8. customRecrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-f82d90aa808c4e5093010fd8e0b90fcd
Source dataset
uspto-grants-1995_12
Patent number
US05474999

Reaction notes

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