N-bromobutanimide → Methyl 2,3,4,5-tetrahydro-7-bromo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate

HRID 1976264ノート

反応式

HRID 1976264 の反応式
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3]1=[O:18].[Br:19]N1C(=O)CCC1=O>C(Cl)Cl>[Br:19][C:10]1[CH:11]=[CH:12][C:6]2[NH:5][CH:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3](=[O:18])[N:2]([CH3:1])[CH2:8][C:7]=2[CH:9]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 11770765Methyl 2,3,4,5-tetrahydro-3-oxo-4-methyl-1H-1,4-benzodiazepine-2-acetate

生成物 1

HCID 22000818Methyl 2,3,4,5-tetrahydro-7-bromo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate収率 93%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
28 °C

実験手順

Methyl 2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate (100 g, 0.4 mole) and n-Bu4 N Br (13 g, 0.04 mole) were added to CH2Cl2 (1.0 liter) and refluxed for 0.5 hr. The reaction mixture was cooled to 28° C. and N-Bromosuccinimide added in small portions (72.8 g, 0.41 mole). The reaction was stirred at ambient temperature for 1.0 hr then washed with 5% NaHCO3 solution (400 ml) then water (2×400 ml) CH2Cl2 (800 ml) was replaced with hexane (800 ml) via ‘put and take’ distillation, the resulting slurry was cooled, filtered and washed with hexane. The product was dried in vacuo to yield the title compound (123 g, 93%). HPLC analysis showed 0.7% residual starting material and 0.7% 7,9-dibromide.

後処理

  1. temperaturerefluxed for 0.5 hr
  2. washthen washed with 5% NaHCO3 solution (400 ml)
  3. distillationdistillation
  4. temperaturethe resulting slurry was cooled
  5. filtrationfiltered
  6. washwashed with hexane
  7. customThe product was dried in vacuo

出典と根拠

ORDレコード
ord-46b139e2410f42f3b70b7f864bbf9d25
出典データセット
uspto-grants-2001_05
特許番号
US06225465B1

反応ノート

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