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

HRID 55200Notes

Reaction equation

HRID 55200 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-f76808df9fd04c8281855a4075fdd1d5
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Reaction notes

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