Ethanol → HCID 59161196、化合物

HRID 545505ノート

反応式

HRID 545505 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 59161196HCID 59161196、化合物収率 81%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-80fb3a01dd5c4a0391d6d7a975dab062
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

読み込み中…