Water → HCID 10787333, compound

HRID 865049Notes

Reaction equation

HRID 865049 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.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH2:32])[CH:20]=[CH:21][C:22]=1[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24].O>CN(C)C(=O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:32][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH:20]=[CH:21][C:22]=1[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:24])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 21480129HCID 21480129, compound

Product 1

HCID 10787333HCID 10787333, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.80 g, 11.4 mmol) in N,N-dimethylacetamide (40 mL) was added thionyl chloride (1.36 g, 11.4 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 3-Methoxy-4-(phenylsulfonyl)benzeneamine (2.00 g, 7.6 mmol) was added in one portion and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the aqueous solution filtered through a pad of Celite. The Celite was washed with methylene chloride (200 mL), the organic extract dried (MgSO4), and the solvent removed in vacuo to yield a brown oil which was purified by flash column chromatography (10% v/v ethyl acetate/methylene chloride). The resulting white solid (2.52 g, 82%) melted at 202°-204° C. 1H-NMR (250 MHz, d6-DMSO): 1.56 (s, 3H, CH3) 3.87 (s, 3H, OCH3) 7.70-7.54 (m, 6H, aromatic+OH) 7.85-7.88 (m, 2H, aromatic) 7.93 (d, 1H, J=8.7 Hz, aromatic) 10.32 (s, 1H, NH). MS (CI, CH4): 404 (M+1).

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. filtrationthe aqueous solution filtered through a pad of Celite
  3. washThe Celite was washed with methylene chloride (200 mL)
  4. extractionthe organic extract
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto yield a brown oil which
  8. customwas purified by flash column chromatography (10% v/v ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-0ad6a9cfcc0f4f0cb2f7a9d7488d3668
Source dataset
uspto-grants-1996_10
Patent number
US05565465

Reaction notes

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