Benzoyl chloride, 3-bromo- → 3-Bromo-N-methoxy-N-methylbenzamide

HRID 30554

反応式

HRID 30554 の反応式
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(C(C)C)CC)(C)C.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>C(Cl)Cl>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([N:4]([O:3][CH3:2])[CH3:5])=[O:20]

参加物

5

反応物 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

生成物 1

HCID 121628753-Bromo-N-methoxy-N-methylbenzamide収率 90.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of N-methoxymethanamine hydrochloride (22.1 g, 228.5 mmol), diisopropyl ethyl amine (63.5 mL, 365.6 mmol) and CH2Cl2 was treated dropwise with 3-bromobenzoyl chloride (15 g, 68.5 mmol) in CH2Cl2, stirred at room temperature for 30 minutes, and concentrated under vacuum. The resultant residue was dispersed in water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (Biotage) using hexanes/EtOAc (2/1) as the eluting solvents to give 3-bromo-N-methoxy-N-methylbenzamide as a tan solid (15.1 g, 90% yield).

後処理

  1. concentrationconcentrated under vacuum
  2. additionThe resultant residue was dispersed in water
  3. extractionextracted with ethyl ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified on silica gel (Biotage)

出典と根拠

ORDレコード
ord-166da1d9e33a4bd8acda9bd0700ddbfe
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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