1,2-Dichloroethane → 3-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide

HRID 594070

반응식

HRID 594070 반응식
C(Cl)CCl.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH2:15][OH:16])[C:9]([OH:11])=O.[F:17][C:18]([F:27])([F:26])[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.O>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH2:15][OH:16])[C:9]([NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([C:18]([F:17])([F:26])[F:27])[CH:20]=1)=[O:11]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 73753-(Trifluoromethyl)anilineHCID 181649HOAtHCID 196884153-Bromo-4-(hydroxymethyl)benzoic acid

생성물 1

HCID 904079633-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide수율 35%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

EDC (1.3 equiv.) was added to a solution of 3-bromo-4-(hydroxymethyl)benzoic acid (1.0 equiv), 3-(trifluoromethyl)aniline (1.1 equiv.), HOAt (1.3 equiv.) in DMF (0.43 M). The mixture was stirred at ambient temperature 3 hrs. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by ISCO(50% EtOAc/Heptane) to yield 3-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide in 35% yield. LC/MS (m/z)=374.0 (MH+), Rt=0.93 min.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed sequentially with 1M aqueous sodium hydroxide and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by ISCO(50% EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-97272b5ef77b4a53bcffe989e86abaa7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242969B2

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