4-Fluorophenylhydrazine hydrochloride → HCID 59161212、化合物

HRID 545500ノート

反応式

HRID 545500 の反応式
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]1>Cl>[F:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:14][C:13]2=1

参加物

4

反応物 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

生成物 1

HCID 59161212HCID 59161212、化合物収率 84.3%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

Combine p-fluorophenylhydrazine hydrochloride (5.00 g, 30.7 mmol) and N-(4-oxo-cyclohexyl)isobutyramide (5.64 g, 30.7 mmol) in ethanolic HCl (125 mL) and heat at reflux under nitrogen for 18 h. Concentrate the reaction in vacuo to remove most of the EtOH, dilute with water and extract with EtOAc. Wash the EtOAc extracts with water and brine, dry over Na2SO4, and evaporate to give 7.1 g (56%) of a beige solid. MS (ES): m/z 275 (M+1); 1H NMR(DMSO-d6): δ 10.79 (s, 1H, NH), 7.81 (d, 1H, J=7.5 Hz), 7.19 (dd, 1H, J=8.6, 4.6 Hz), 7.07 (d, 1H, J=10.1 Hz), 6.79 (dt, 1H, J=8.9, 1.8 Hz), 4.00 (m, 1H), 2.85 (dd, 1H, J=15.0, 5.3 Hz), 2.76 (m, 2H), 2.39 (m, 2H), 1.93 (m, 1H), 1.75 (m, 1H), 0.99 (d, 6H, J=6.6 Hz).

後処理

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. customto remove most of the EtOH
  5. additiondilute with water
  6. extractionextract with EtOAc
  7. washWash the EtOAc
  8. dry with materialdry over Na2SO4
  9. customevaporate

出典と根拠

ORDレコード
ord-b0ff8d24e73042a5ba5bd6ac7d073c25
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

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