Ammonia → Medazepam

HRID 441940

반응식

HRID 441940 반응식
[BH4-].[Na+].B(F)(F)F.CCOCC.[CH3:12][N:13]1[C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:16][CH2:15][C:14]1=O.Cl.N>O1CCCC1>[CH3:12][N:13]1[C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[C:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:16][CH2:15][CH2:14]1

참가 물질

7

반응물 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3016DiazepamHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydride

생성물 1

HCID 4041Medazepam수율 103%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of 2.28 g of sodium borohydride in 35ml of tetrahydrofuran was added dropwise with stirring a solution of 13.0 g of boron trifluoride etherate in 10ml of tetrahydrofuran below 10° C, and the mixture was stirred at room temperature for 45 minutes. To the mixture was added dropwise solution of 1.43 g of 1-methyl-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 10 ml of tetrahydrofuran at -15° to -12.5° C over a period of 5 minutes, and then the mixture was stirred at =15° C for 22 hours. The reaction mixture was poured into 100 ml of ice-water, and then 20 ml of concentrated hydrochloric acid was added. The mixture was refluxed for 30 minutes, then cooled, and neutralized with concentrated ammonia. The tetrahydrofuran layer was separated, and the aqueous layer was extracted with ether. The combined organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 1.4 g of 1-methyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepine.

후처리

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at =15° C for 22 hours
  3. temperatureThe mixture was refluxed for 30 minutes
  4. temperaturecooled
  5. customThe tetrahydrofuran layer was separated
  6. extractionthe aqueous layer was extracted with ether
  7. washThe combined organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-f477172c64e844b98d04e50fc6afdfa7
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04044003

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