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

HRID 374872
Notes
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Reaction equation

HRID 374872 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8058
Hexane
Solvent
HCID 31374DimethylacetamideSolvent
HCID 21881112Ethyl ether methylene chlorideSolvent

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-8a01073b36c24dc79dbb4f0545aeedcb
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05482969

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes