2-Bromoethanol → 11b-(2-Chlorophenyl)-7-(2-hydroxyethyl)-10-nitro-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one

HRID 2071950

반응식

HRID 2071950 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[O:25][CH2:24][CH2:23][N:9]1[CH2:10][C:11](=[O:22])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=12.[H-].[Na+].Br[CH2:29][CH2:30][OH:31]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[O:25][CH2:24][CH2:23][N:9]1[CH2:10][C:11](=[O:22])[N:12]([CH2:29][CH2:30][OH:31])[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=12

참가 물질

5

반응물 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 1231790211b-(2-chlorophenyl)-10-nitro-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one

생성물 1

HCID 2140998311b-(2-Chlorophenyl)-7-(2-hydroxyethyl)-10-nitro-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1.5 g (0.0041 M) of 11b-(2-chlorophenyl)-10-nitro-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one in 30 ml of dry N,N-dimethylformamide was treated with 0.34 g (0.008 M) of a 57% dispersion of sodium hydride in mineral oil with stirring under nitrogen. After 30 min, 1.5 g (0.012 M) of 2-bromoethanol was added and the reaction was heated to 90° for 3 hr. The solvent was removed under vacuum, and the residue was dissolved in 50 ml of dichloromethane which was then washed with 50 ml of water, 25 ml of a saturated solution of brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was crystallized from ether, and recrystallized from a mixture of dichloromethane and methanol to give the product as pale yellow prisms, m.p. 185°-190°(dec.).

후처리

  1. temperaturethe reaction was heated to 90° for 3 hr
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in 50 ml of dichloromethane which
  4. washwas then washed with 50 ml of water, 25 ml of a saturated solution of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was crystallized from ether
  8. customrecrystallized from a mixture of dichloromethane and methanol

출처 및 근거

ORD 기록
ord-b37250670fcf406dbee6e1c8c5d934e9
출처 데이터셋
uspto-grants-1977_09
특허 번호
US04049667

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