Water → HCID 10739955, compound

HRID 865256Notes

Reaction equation

HRID 865256 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][N: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][N: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 10730311HCID 10730311, compound

Product 1

HCID 10739955HCID 10739955, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.79 g, 11.3 mmol) in N,N-dimethylacetamide (20 mL) was added thionyl chloride (1.34 g, 11.3 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 3-Methoxy-4-(4-pyridylsulfonyl)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 Celite. The Celite was washed with methylene chloride (100 mL), the methylene chloride solution dried (MgSO4) and concentrated in vacuo to an off-white solid. Trituration with ethyl ether yielded the title propanamide as a white solid (1.65 g, 54%); mp 238°-240° C. 1H-NMR (250 MHz, d6-DMSO): 1.58 (s, 3H, CH3) 3.70 (s, 3H, OCH3) 7.60 (s, 1H, OH) 7.71 (d, 1H, J=4.6 Hz, aromatic) 7.75-7.79 (m, 3H, aromatic) 7.96 (d, 1H, J=8.8 Hz, aromatic) 8.85 (dd, 2H, J=4.6, 1.1 Hz, aromatic) 10.39 (s, 1H, NH). MS (CI, CH4): 405 (M+1).

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. filtration-the aqueous solution filtered through Celite
  3. washThe Celite was washed with methylene chloride (100 mL)
  4. dry with materialthe methylene chloride solution dried (MgSO4)
  5. concentrationconcentrated in vacuo to an off-white solid

Sources & evidence

ORD record
ord-802f4a1b46b24bf3a37a52264b72e493
Source dataset
uspto-grants-1996_10
Patent number
US05565477

Reaction notes

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