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

HRID 1976264노트

반응식

HRID 1976264 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
28 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-46b139e2410f42f3b70b7f864bbf9d25
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225465B1

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