Water → HCID 10760503, compound

HRID 2259694Notes

Reaction equation

HRID 2259694 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.[NH2:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])=[C:18]([OH:30])[CH:17]=1.O>CN(C)C(=O)C>[OH:30][C:18]1[CH:17]=[C:16]([NH:15][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH:29]=[CH:28][C:19]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 21480108(4-Amino-2-hydroxyphenyl)(phenyl)methanone

Product 1

HCID 10760503HCID 10760503, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.78 g, 4.9 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.59 g, 4.9 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-Amino-2-hydroxybenzophenone (0.70 g, 3.3 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 decanted from an oily precipitate which was dissolved in methylene chloride, dried (MgSO4) and concentrated in vacuo to yield a brown oil. Purification by flash column chromatography (5% v/v ethyl acetate/methylene chloride) yielded the title propanamide as a white solid (0.83 g, 71%); mp 173°-175° C. 1H-NMR (250 MHz, CDCl3): 1.74 (s, 3H, CH3) 3.49 (s, 1H, OH) 7.14 (dd, 1H, J=8.7, 2.2 Hz, aromatic) 7.28 (d, 1H, J=2.1 Hz, aromatic),7.46-7.65 (m, 6H, aromatic) 8.49 (s, 1H, NH) 12.3 (s, 1H, phenolic OH). MS (CI, CH4): (M+1). Analysis for C16H14F3NO4 : Calculated: C, 57.79; H, 3.99; N, 3.96. Found: C, 57.66; H, 4.05; N, 3.95.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. customthe aqueous solution decanted from an oily precipitate which
  3. dissolutionwas dissolved in methylene chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a brown oil
  7. customPurification by flash column chromatography (5% v/v ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-7ef1f6b77ad849929a0de48ee2f025b3
Source dataset
uspto-grants-1995_12
Patent number
US05474999

Reaction notes

Loading…