Nordiazepam → 7-chloro-1,3-dihydro-1-(2,2-dimethoxyethyl)-5-phenyl-2H-1,4-benzodiazepine-2-one

HRID 328109

반응식

HRID 328109 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[H-].[Na+].[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25]Br>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:25][CH:24]([O:27][CH3:28])[O:23][CH3:22])[C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

참가 물질

5

반응물 3

HCID 2997NordiazepamHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

생성물 1

HCID 123809087-chloro-1,3-dihydro-1-(2,2-dimethoxyethyl)-5-phenyl-2H-1,4-benzodiazepine-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 27.1 g. (0.1 mole) of 7-chloro-1,3 -dihydro-5-phenyl-2H-1,4-benzodiazepine-2-one in 300 ml. of dry dimethylformamide was added 4.6 g. (0.11 mole) of 57% sodium hydride in mineral oil, under nitrogen and with continuous stirring. After stirring one hour at room temperature, 25.4 g. (0.15 mol) of redistilled bromoacetaldehyde dimethylacetal in 10 ml. of dimethylformamide was added and the reaction mixture is kept at 100° C. with stirring during 16 hours. The mixture was then concentrated in vacuo to one-half the volume, well shaken with ice water and extracted with methylene chloride. The extract was washed with water, dried over Na2SO4 and evaporated at 25° C. and 0.2 mm.Hg pressure giving a brown oil which was crystallized from 2-propanol yielding 26.2 g. (73% of light brown crystals m.p. 115-117° C. A sample chromatographed on silica gel, eluted with 2% methanol-98% chloroform, evaporated in vacuo, and crystallized from 2-propanol gave 7-chloro -1,3-dihydro-1-(2,2-dimethoxyethyl)-5-phenyl-2H-1,4 -benzodiazepine-2-one of melting point 117° to 119° C.

후처리

  1. customis kept at 100° C.
  2. stirringwith stirring during 16 hours
  3. concentrationThe mixture was then concentrated in vacuo to one-half the volume
  4. stirringwell shaken with ice water
  5. extractionextracted with methylene chloride
  6. washThe extract was washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated at 25° C.
  9. custom0.2 mm.Hg pressure giving a brown oil which
  10. customwas crystallized from 2-propanol yielding 26.2 g
  11. customA sample chromatographed on silica gel
  12. washeluted with 2% methanol-98% chloroform
  13. customevaporated in vacuo
  14. customcrystallized from 2-propanol

출처 및 근거

ORD 기록
ord-e1839d23810445e28933730f9b4306be
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04016165

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