Water → 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

HRID 67388노트

반응식

HRID 67388 반응식
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([NH2:19])=O)=[C:4]2[CH2:3]1.O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]#[N:19])=[C:4]2[CH2:3]1

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 205153215,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide

생성물 1

HCID 139845425-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

0.5 g of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide is heated to reflux while stirring for 40 hours together with 0.5 g of Sicapent in 150 ml of toluene. The mixture is treated with a 0.5 g portion of Sicapent after 16 hours, 19 hours and 24 hours. The mixture is subsequently cooled and treated with water. The mixture is adjusted to pH 9 with 28 percent sodium hydroxide. After separation of the organic phase, the alkaline-aqueous phase is extracted twice with 250 ml of ethyl acetate each time. The organic extracts are washed twice with saturated sodium chloride solution, dried and evaporated. After crystallisation of the residue from methylene chloride/hexane, there is recovered a portion of unreacted starting material. The mother liquor is evaporated and chromatographed on 100 g of silica gel while eluting with ethyl acetate and alcohol. After recrystallisation of the thus-obtained substance from acetone, there is obtained 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[ 1,5-a][1,4]benzodiazepine-3-carbonitrile of melting point 184°-185° C.

후처리

  1. temperatureto reflux
  2. additionThe mixture is treated with a 0.5 g portion of Sicapent after 16 hours, 19 hours and 24 hours
  3. temperatureThe mixture is subsequently cooled
  4. customAfter separation of the organic phase
  5. extractionthe alkaline-aqueous phase is extracted twice with 250 ml of ethyl acetate each time
  6. washThe organic extracts are washed twice with saturated sodium chloride solution
  7. customdried
  8. customevaporated
  9. customAfter crystallisation of the residue from methylene chloride/hexane, there
  10. customis recovered a portion
  11. customThe mother liquor is evaporated
  12. customchromatographed on 100 g of silica gel
  13. washwhile eluting with ethyl acetate and alcohol
  14. customAfter recrystallisation of the thus-obtained substance from acetone

출처 및 근거

ORD 기록
ord-270558e62e564da99d54e7a40a646e5d
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346031

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