Triethylamine → 5,6-Dihydro-6-(4-nitrobenzoyl)-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 1420028Notes

Reaction equation

HRID 1420028 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[NH:8][CH2:9][CH2:10][C:4]2=[N:3][N: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]>ClCCl>[N+:22]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([N:8]2[C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[N:5]3[CH:1]=[N:2][N:3]=[C:4]3[CH2:10][CH2:9]2)=[O:30])=[CH:32][CH:33]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 218370045,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Product 1

HCID 218372105,6-Dihydro-6-(4-nitrobenzoyl)-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3 mmol of 5,6-dihydro-4H-[1,2,4]-triazolo[4,3-a][1,5]benzodiazepine in 10 ml of dichloromethane under argon is added 5 mmol of triethylamine. To the mixture is added dropwise 3.3 mmol of 4-nitrobenzoyl chloride in 3 ml of dichloromethane. The mixture is stirred at room temperature 3 hours and then washed with water, aqueous NaHCO3 and brine. The organic layer is dried (Na2SO4) and the solvent removed under vacuum. The residue is purified by chromatography on silica gel to give the desired product as a solid.

Workup

  1. washwashed with water, aqueous NaHCO3 and brine
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent removed under vacuum
  4. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a7d15027ce02457186f5f0a8d11ca20e
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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