Ammonia → 1-methyl-5-phenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepine

HRID 441941

반응식

HRID 441941 반응식
B#B.[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:7][CH2:6][C:5]1=O.Cl.N>O1CCCC1>[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=2[C:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:7][CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4496NimetazepamHCID 6328200Diboron

생성물 1

HCID 214160441-methyl-5-phenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepine수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-8 °C

실험 절차

To a solution of 30 ml of 1.07 M diborane in tetrahydrofuran was added with stirring 1.48 g of 1-methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-one at -13° to -8° C, and the mixture was further stirred at -8° C for 1 hour and 45 minutes. The reaction mixture was poured into ice-water, and 20 ml of concentrated hydrochloric acid was added. The mixture was refluxed for one hour. After cooling, the resultant solution was neutralized with 28%-aqueous ammonia, and extracted with chloroform. The chloroform extracts were washed with water and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in a 20%-solution of hydrochloric acid in ethyl alcohol, and refluxed for 10 minutes. The alcohol was removed by distillation under reduced pressure, and the residue was distributed between water and chloroform. The chloroform layer was separated, washed with water, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.34 g of 1-methyl-5-phenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepine, which was recrystallized from isopropyl alcohol to yield yellow flakes melting at 186° to 187° C.

후처리

  1. additionwas added
  2. temperatureThe mixture was refluxed for one hour
  3. temperatureAfter cooling
  4. extractionextracted with chloroform
  5. washThe chloroform extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in a 20%-solution of hydrochloric acid in ethyl alcohol
  9. temperaturerefluxed for 10 minutes
  10. customThe alcohol was removed by distillation under reduced pressure
  11. customThe chloroform layer was separated
  12. washwashed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe solvent was removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-566be60e615641caaeae75280a5c1186
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04044003

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