Ethanol → HCID 59161196, 화합물

HRID 545505노트

반응식

HRID 545505 반응식
C(Cl)(=O)C.C(O)C.Cl.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17]N)=[CH:13][CH:12]=1.O=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[NH:17][C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])[CH2:22][C:21]2=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

생성물 1

HCID 59161196HCID 59161196, 화합물수율 81%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Add acetyl chloride (8.5 mL, 120 mmol) to absolute ethanol (30 mL) and stir for 1 h. Add 4-methoxyphenylhydrazine hydrochloride (1.74 g, 10 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (Preparation 2) (1.83 g, 120 mmol) and reflux with stirring for 56 h. Cool to room temperature, dilute with ethyl acetate (100 mL) and wash with sodium bicarbonate solution (2×50 mL), brine, dry (MgSO4), filter and concentrate in vacuo. Dissolve the residue in dichloromethane and pass over a silica pad, eluting with 20% ethyl acetate/dichloromethane to obtain 2.32 g of a solid. Triturate the solid in diethyl ether with a small amount of dichloromethane, filter and dry under house vacuum to obtain 2.14 g (75%) of an off-white solid. MS (ES): m/z 287 (M+1), 285 (M−1); 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.13 (d, 1H, J=8.8 Hz), 6.85 (s, 1H), 6.64 (dd, 1H, J=8.8, 2.2 Hz), 4.02 (m, 1H), 3.75 (m, 3H), 2.90 (dd, 1H, J=15.0, 5.3 Hz), 2.78 (m, 2H), 2.42 (m, 2H), 1.96 (m, 1H), 1.79 (m, 1H), 1.03 (d, 6H, J=6.6 Hz).

후처리

  1. stirringwith stirring for 56 h
  2. washwash with sodium bicarbonate solution (2×50 mL), brine
  3. dry with materialdry (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. dissolutionDissolve the residue in dichloromethane
  7. washpass over a silica pad, eluting with 20% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-80fb3a01dd5c4a0391d6d7a975dab062
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935722B2

반응 노트

불러오는 중…