Propylamine → 3-bromo-N-propylbenzamide

HRID 30582

反応式

HRID 30582 の反応式
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH:4][CH2:1][CH2:2][CH3:3])=[O:17]

参加物

6

反応物 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 516892Sodium Bicarbonate

生成物 1

HCID 31186553-bromo-N-propylbenzamide収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

A mixture of N-propyl amine (0.33 mL, 4.1 mmol) and triethylamine (0.83 mL, 5.8 mmol) in methylene chloride was cooled to −5° C., treated with 3-bromobenzoyl chloride (1 g, 4.5 mmol), warmed to room temperature, stirred at room temperature for 1 h, poured into aqueous sodium bicarbonate and extracted with methylene chloride. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by flash chromatography on silica gel, 2:1 hexane/ethyl acetate as eluent, to give 3-bromo-N-propyl-benzamide as a white solid, 0.74 g (67% yield); 1H NMR (DMSO-d6) δ 0.8 (t, 3H); 1.5 (m, 2H); 3.2 (t, 2H); 7.4 (t, 1H); 7.6 (d, 1H), 7.8 (d, 1H); 7.9 (s, 1H); 8.5 (b, 1H); MS [(+)ESI] m/z 242[M−H]+.

後処理

  1. temperaturewarmed to room temperature
  2. extractionextracted with methylene chloride
  3. washwashed sequentially with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by flash chromatography on silica gel, 2:1 hexane/ethyl acetate as eluent

出典と根拠

ORDレコード
ord-fb1e271f2d5641358ec23bf5560de3df
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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