Benzylamine → 3-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol

HRID 1181153ノート

反応式

HRID 1181153 の反応式
[Br:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[C:5](Br)[N:4]([CH2:11][CH2:12][CH2:13][OH:14])[N:3]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[CH2:15]([NH:22][C:5]1[N:4]([CH2:11][CH2:12][CH2:13][OH:14])[N:3]=[C:2]([Br:1])[C:6]=1[N+:7]([O-:9])=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

4

反応物 2

HCID 7504BenzylamineHCID 231041703-(3,5-Dibromo-4-nitropyrazol-1-yl)propan-1-ol

生成物 1

HCID 130072283-(5-Benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3-(3,5-dibromo-4-nitropyrazol-1-yl)propan-1-ol (3-2) (17.1 g, 52 mmol), EtOH (100 ml) and benzylamine (27.9 g, 260 mmol) was refluxed for 15 hours. The reaction medium was concentrated to the maximum under reduced pressure. The highly viscous residue was suspended in EtOAc (100 ml) and EtOH (100 ml). The organic phase was washed with NaCl solution (10%, 100 ml) and then dried over Na2SO4. After evaporating off the solvent under reduced pressure, an orange-colored oil was obtained (13.6 g), which was subsequently purified by column chromatography (gradient: 10%/90% EtOAc/hexane to 40%/60% EtOAc/hexane) in order to obtain, after evaporating off the solvent, the 3-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propan-1-ol in the form of a yellow solid (8.8 g, 48%).

後処理

  1. temperaturewas refluxed for 15 hours
  2. concentrationThe reaction medium was concentrated to the maximum under reduced pressure
  3. washThe organic phase was washed with NaCl solution (10%, 100 ml)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporating off the solvent under reduced pressure
  6. customan orange-colored oil was obtained (13.6 g), which
  7. customwas subsequently purified by column chromatography (gradient: 10%/90% EtOAc/hexane to 40%/60% EtOAc/hexane) in order
  8. customto obtain
  9. customafter evaporating off the solvent

出典と根拠

ORDレコード
ord-4e7d778970bb47008148702d2a8cb166
出典データセット
uspto-grants-2007_10
特許番号
US07285136B2

反応ノート

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