1,2-Dichloroethane → 4-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

HRID 579596

반응식

HRID 579596 반응식
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:32][NH:33][O:34][CH3:35].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:35][O:34][N:33]([CH3:32])[C:18]([CH:15]1[CH2:16][CH2:17][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=2)[CH2:13][CH2:14]1)=[O:20]

참가 물질

9

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

생성물 1

HCID 885771284-(4-Chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

EDC (3.21 g, 16.8 mmol) was added portionwise to a stirred solution of 4-(4-chlorophenyl)-cyclohexanecarboxylic acid (2.0 g, 8.4 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (1.63 g, 16.8 mmol) in dichloromethane (40 mL). Triethylamine (3.4 g, 4.7 mL, 33.5 mmol) was added dropwise, and the reaction mixture was stirred at room temperature. After stirring overnight the reaction mixture was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 4-(4-chlorophenyl)-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.85 g. 78%); MS (+CI): m/z for C15H20ClNO2: expected 281.1. found 282.2 (M+H)+.

후처리

  1. stirringAfter stirring overnight the reaction mixture
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b3567bb806dc48f794504e860688111f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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