Water → N-(4-Benzoyl-2-methylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

HRID 1075380Notes

Reaction equation

HRID 1075380 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])=[CH:18][C:17]=1[CH3:30].O>CN(C)C(=O)C.CCCCCC.C(OCC)C.ClCCl>[C:20]([C:19]1[CH:28]=[CH:29][C:16]([NH:15][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:17]([CH3:30])[CH:18]=1)(=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 962WaterHCID 21052Benzophenone, 4-amino-3-methyl-HCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Product 1

HCID 9819831N-(4-Benzoyl-2-methylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 31374DimethylacetamideSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Conditions

Temperature
-12.5 °C

Procedure

To a solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.11 g) in N,N-dimethylacetamide (15 mL) at -20° C. was added thionyl chloride (0.84 g) and the mixture was allowed to stir at -10 to -15° C. for 1 hour. 4-Amino-3-methylbenzophenone (1.00 g) was added in one portion and the reaction mixture was stirred at room temperature overnight. The mixture was poured into water and the resultant gummy solid was collected by filtration. The solid was dissolved in methylene chloride, dried and evaporated to give a brown oil. Chromatography, with diethyl ether:dichloromethane (2:98) as the eluent, gave a white foam which was stirred with hexane for two hours. The title compound was collected by filtration as a white solid (1.04 g); mp 123-124° C.; MS: m/z=352(M+1); NMR: 1.61 (s,3), 2.28 (s,3), 7.54-7.61 (m,3) 7.66-7.74 (m,6) 9.73 (s,1). Analysis for C18H16F3NO3 : Calculated: C, 61.54; H, 4.59; N, 3.99; Found: C, 61.53; H, 4.73; N, 4.01.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationthe resultant gummy solid was collected by filtration
  3. dissolutionThe solid was dissolved in methylene chloride
  4. customdried
  5. customevaporated
  6. customto give a brown oil
  7. filtrationThe title compound was collected by filtration as a white solid (1.04 g)

Sources & evidence

ORD record
ord-502a2b79029c401aa7d64da2d92c3882
Source dataset
uspto-grants-1999_05
Patent number
US05900432

Reaction notes

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