1,2-Dichloroethane → 5-Acetyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

HRID 25026

반응식

HRID 25026 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.C1C=CC2N(O)N=NC=2C=1.O.C(Cl)CCl.[F:30][C:31]([F:41])([F:40])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>C(Cl)Cl.CN(C=O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([NH:37][CH2:36][C:35]1[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:40])[F:41])=[CH:39][CH:38]=1)=[O:7])(=[O:14])[CH3:13]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 768044-(Trifluoromethyl)benzylamineHCID 189545915-Acetyl-2-methoxybenzoic acid

생성물 1

HCID 219645355-Acetyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-Methoxy-5-acetylbenzoic acid (Step B, 2.5 g, 12.8 mmol), HOBt.H2O (2.08 g, 15.4 mmol), and EDC (3.70 g, 19.3 mmol) in CH2Cl2 (20 ml) and DMF (5 ml) was added 4-(Trifluoromethyl)benzylamine (2.48 g, 14.1 mmol), and the mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure and then redissolved in ethyl acetate. The organic layer was washed with 3% K2CO3, 1 N HCl, and brine, dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionredissolved in ethyl acetate
  3. washThe organic layer was washed with 3% K2CO3, 1 N HCl, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe purification

출처 및 근거

ORD 기록
ord-6aed3cfb206a4de4961a6b5711e6cae0
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858602B2

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