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

HRID 1598261

반응식

HRID 1598261 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 treated 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. additionThe combined organic layers are treated with activated carbon
  11. filtrationfiltered through MgSO4
  12. customThe filtrate is evaporated in vacuo to a tan foam which
  13. 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-0d6c1a8d1c6f438fb79a3713057c46de
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736540

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