Sodium hydride → N-[4-(5H-Imidazo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-2 4-dichlorobenzamide

HRID 3605

반응식

HRID 3605 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][N:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>O1CCOCC1>[N:21]1[CH:20]=[CH:19][N:11]2[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:27]=4[Cl:26])=[CH:23][CH:22]=3)=[O:7])[CH2:9][C:10]=12

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 666452,4-Dichlorobenzoyl chlorideHCID 2183708710,11-Dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c]-[1,4]benzodiazepine

생성물 1

HCID 21837155N-[4-(5H-Imidazo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-2 4-dichlorobenzamide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매3회

실험 절차

A slurry of 0.330 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 15 ml of dioxane is stirred and warmed slightly to obtain a nearly complete solution. The reaction mixture is cooled to room temperature and 43 mg of sodium hydride in oil added. The mixture is warmed slightly. Gas evolution stops in a few minutes. The reaction mixture is cooled to room temperature and 153 μl of 2,4-dichlorobenzoyl chloride in 2.5 ml of dioxane added. An additional 3.5 ml of dioxane is added and the reaction mixture stirred at room temperature for 2 days. The volatiles are evaporated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is separated and the aqueous phase extracted with chloroform two more times. The combined organic layers are trated with activated carbon and filtered through MgSO4. The filtrate is evaporated in vacuo to a tan foam which is purified by flash chromatography on silica gel by elution with CHCl3 and 3-7% CH3 OH in chloroform to give 310 mg of tan foam.

후처리

  1. temperaturewarmed slightly
  2. customto obtain a nearly complete solution
  3. temperatureThe mixture is warmed slightly
  4. waitGas evolution stops in a few minutes
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customThe volatiles are evaporated in vacuo to a residue which
  7. customis partitioned between water and chloroform
  8. customThe organic layer is separated
  9. extractionthe aqueous phase extracted with chloroform two more times
  10. filtrationfiltered through MgSO4
  11. customThe filtrate is evaporated in vacuo to a tan foam which
  12. customis purified by flash chromatography on silica gel by elution with CHCl3 and 3-7% CH3 OH in chloroform

출처 및 근거

ORD 기록
ord-2645c2c262564c698b845595cc95d126
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733905

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