Triethylamine → 6,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

HRID 440047

반응식

HRID 440047 반응식
[CH:1]1[C:11]2[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C(Cl)Cl>[Cl:22][C:23]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][C:24]=1[C:25]([N:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[N:10]2[CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8][CH2:7]1)=[O:26]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

생성물 1

HCID 218370306,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine수율 105.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 0.28 g of 6,7-dihydro-5H-pyrrolo-[1,2-a][1,5]benzodiazepine in 6 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.50 g of 2-chloro-4-nitrobenzoyl chloride in 0.5 ml of methylene chloride. The reaction mixture is stirred at room temperature for 1 hour then quenched with 5 ml of saturated NaHCO3. The methylene chloride is evaporated in vacuo and the residue is diluted with 5 ml of water and extracted with 20 ml of ethyl acetate. The organic layer is separated, washed with saturated NaHCO3 and brine, dried with Na2SO4 and evaporated in vacuo to give 0.59 g of a yellow foam which is triturated with ether-hexanes to give 0.56 g of the desired product as off-white solid. MS(CI): 368(M+H) (Cl35) 370(M+H) (Cl37)

후처리

  1. customthen quenched with 5 ml of saturated NaHCO3
  2. customThe methylene chloride is evaporated in vacuo
  3. additionthe residue is diluted with 5 ml of water
  4. extractionextracted with 20 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with saturated NaHCO3 and brine
  7. dry with materialdried with Na2SO4
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-1bfa38b3758b4decbcfcf30ec56ede1d
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516774

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