Water → N-(4-benzoyl-2-fluorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

HRID 1075381Notes

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[F:30].O>CN(C)C(=O)C>[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]([F:30])[CH:18]=1)(=[O:21])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -12.5 °C

Procedure

To a solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (4.51 g) in N,N-dimethylacetamide (60 mL) at -20° C. was added thionyl chloride (3.39 g) and the mixture was allowed to stir at -10 to -15° C. for 1 hour. 4-Amino-3-fluorobenzophenone (4.00 g) was added in one portion and the reaction mixture was stirred at room temperature overnight. The mixture was poured into water and the aqueous solution was decanted. The remaining oily precipitate was dissolved in dichloromethane, dried, and evaporated to yield a tan solid. Recrystallization from dichloromethane and hexanes yielded the title compound as a white solid (5.43 g); mp 138-139° C.; MS: m/z=356(M+1); NMR: 1.62 (s,3), 7.56-7.64 (m,4), 7.70 (d,1, J=6.5), 7.75 (d,2, J=8.0), 7.82 (s,1), 8.01 (t,1, J=7.9), 9.39 (s,1). Analysis for C17H13F4NO3 : Calculated: C, 57.47; H, 3.69; N, 3.94; Found: C, 57.51; H, 3.60; N, 3.93.

Workup

stirringthe reaction mixture was stirred at room temperature overnight
customthe aqueous solution was decanted
dissolutionThe remaining oily precipitate was dissolved in dichloromethane
customdried
customevaporated
customto yield a tan solid
customRecrystallization from dichloromethane and hexanes

Sources & evidence

ORD record: ord-017883db8fb942a2aa53379c848480c3
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05900432

Reaction notes

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