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

HRID 1075381노트

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HRID 1075381 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 107750394-Amino-3-fluorobenzophenone

생성물 1

HCID 9841562N-(4-benzoyl-2-fluorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide수율 82.2%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
-12.5 °C

실험 절차

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.

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customthe aqueous solution was decanted
  3. dissolutionThe remaining oily precipitate was dissolved in dichloromethane
  4. customdried
  5. customevaporated
  6. customto yield a tan solid
  7. customRecrystallization from dichloromethane and hexanes

출처 및 근거

ORD 기록
ord-017883db8fb942a2aa53379c848480c3
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05900432

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