Benzyl Bromide → 1-benzyl-1H-pyrazol-3-amine

HRID 883047

反応式

HRID 883047 の反応式
[NH:1]1[CH:5]=[CH:4][C:3]([N:6]2C(=O)C3C(=CC=CC=3)C2=O)=[N:2]1.[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:1]1[CH:5]=[CH:4][C:3]([NH2:6])=[N:2]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178514958HCID 178514958、化合物

生成物 1

HCID 15086161-benzyl-1H-pyrazol-3-amine収率 32%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

3.1 2-(1H-Pyrazole-3-yl)-isoindole-1,3-dione (11.7 mmol) is added to a suspension of NaH (2 eq.) in DMF at 0° C. Benzylbromide (1 eq.) is added and the reaction is stirred 15 h at 50° C. The solvent is removed in vacuo. Hydrazine hydroxide (10 ml) and ethanol (20 ml) are added and the reaction is stirred 17 hours at 120° C. The precipitate is filtered and the solvent is removed in vacuo. The residue is suspended in dichloromethane and filtrated. The solvent of the filtrate is removed in vacuo. The remaining residue is purified via column chromatography (Ethyl acetate/methanol). 1-Benzyl-1H-pyrazole-3-ylamine is isolated as a yellow powder in a yield of 32%; HPLC (Method B): 2.45 min; LC-MS (Method B): 1.203 min, 174.15 (M+H+);

後処理

  1. customThe solvent is removed in vacuo
  2. additionHydrazine hydroxide (10 ml) and ethanol (20 ml) are added
  3. stirringthe reaction is stirred 17 hours at 120° C
  4. filtrationThe precipitate is filtered
  5. customthe solvent is removed in vacuo
  6. filtrationfiltrated
  7. customThe solvent of the filtrate is removed in vacuo
  8. customThe remaining residue is purified via column chromatography (Ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-d65f0c7dc5fa45feb0aaf321b69d9ab7
出典データセット
uspto-grants-2012_08
特許番号
US08236824B2

関連ノート

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