Methanamine, N-methoxy-, hydrochloride (1:1) → 5-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamide

HRID 576332ノート

反応式

HRID 576332 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.[CH3:15][NH:16][O:17][CH3:18]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([N:16]([O:17][CH3:18])[CH3:15])=[O:8]

参加物

4

反応物 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 867140435-Bromo-2-chloro-3-methoxybenzoyl chloride

生成物 1

HCID 867140445-Bromo-2-chloro-N,3-dimethoxy-N-methylbenzamide収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of acid chloride 59 (3.41 g, 14.3 mmol) in CH2Cl2 (70 mL) was added dropwise N,O-dimethylhydroxylamine hydrochloride (4.18 g, 42.9 mmol) at 0° C. under an atmosphere of nitrogen. Then, TEA (12.0 mL, 85.8 mmol) was added to the mixture at 0° C. After being stirred for 18 hours, the mixture was partitioned between EtOAc (150 mL) and water (100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 60 (3.45 g, 80%) as a white solid.

後処理

  1. customthe mixture was partitioned between EtOAc (150 mL) and water (100 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-126abd24411a41fa83edc91d8f1b3539
出典データセット
uspto-grants-2015_05
特許番号
US09034921B2

反応ノート

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