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

HRID 1740005Notes

Reaction equation

HRID 1740005 reaction equation
[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.[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl.C(OCC)(=O)C>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([N:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[N:10]3[CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7]2)=[O:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 123593416,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Product 1

HCID 218371116,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 mmol of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 30 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are re- moved in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid.

Workup

  1. customfollowed by ice bath
  2. temperaturecooling
  3. additionaddition
  4. customthe ice bath is removed
  5. customto give a residue which
  6. washThe solution is washed with water, 2N citric acid, NaHCO3, and brine
  7. dry with materialThe reaction mixture is dried with Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give a solid which
  11. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e8ed180ae7ec4eefaf62bd7c89d12319
Source dataset
uspto-grants-1999_10
Patent number
US05968930

Reaction notes

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