Sulfuric Acid → 6-phenyl-4H-s-triazolo[4,3-a][1,4-]benzodiazepine

HRID 1764531Notes

Reaction equation

HRID 1764531 reaction equation
[NH:1]([C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]=1)[NH2:2].[CH:20]([O-])([O-])OCC.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[C:10]1([C:7]2[C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=3[N:4]3[CH:20]=[N:2][N:1]=[C:3]3[CH2:9][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 126123892-hydrazino-5-phenyl-3H-1,4-benzodiazepineHCID 53630039Ethylorthoformate

Product 1

HCID 125625186-phenyl-4H-s-triazolo[4,3-a][1,4-]benzodiazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1 part of 2-hydrazino-5-phenyl-3H-1,4-benzodiazepine, prepared in Example 3, 2 parts by volume of ethyl orthoformate and 20 parts by volume of ethanol, 0.44 part by volume of concentrated sulfuric acid is added dropwise with ice-cooling. The mixture is stirred at room temperature for 30 minutes and neutralized with saturated aqueous sodium bicarbonate. The resulting oily substance is extracted with methylene chloride. The methylene chloride layer is washed with water, dried over sodium sulfate and the solvent is evaporated, whereby 6-phenyl-4H-s-triazolo [4,3-a] [1,4] benzodiazepine is yielded as crystals. Recrystallization from a mixture of acetone and n-hexane yields colorless needles melting at 195° C to 196° C.

Workup

  1. additionis added dropwise with ice-
  2. temperaturecooling
  3. extractionThe resulting oily substance is extracted with methylene chloride
  4. washThe methylene chloride layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d75dd46618774ce4b021bb57bed51574
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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