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

HRID 440047

Reaktionsgleichung

Reaktionsgleichung von HRID 440047
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 218370306,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepineAusbeute 105,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1bfa38b3758b4decbcfcf30ec56ede1d
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516774

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