Sulfuric Acid → 1H-1,4-Benzodiazepine

HRID 1764516Notes

Reaction equation

HRID 1764516 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](NN)[CH2:9][N:8]=[C:7](C3C=CC=CC=3)[C:6]=2[CH:20]=1.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>>[NH:11]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:20][C:6]=2[CH:7]=[N:8][CH:9]=[CH:10]1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 1484311H-1,4-Benzodiazepine

Procedure

To a suspension of 2.84 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in 50 parts by volume of acetic anhydride is added 1 part by volume of concentrated sulfuric acid. The resulting solution is left standing at room temperature for 1 hour, poured in ice-water, neutralized with sodium bicarbonate and extracted with methylene chloride. The methylene chloride extract is washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue is recrystallized from a mixture of acetone and n-hexane to give 8-chloro-1-methyl-6-phenyl-4H-s-triazolo [4,3-a]][1,4] benzodiazepine as colorless needles. Melting point: 224° C to 225° C.

Workup

  1. waitThe resulting solution is left
  2. extractionextracted with methylene chloride
  3. extractionThe methylene chloride extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfollowed by evaporation of the solvent
  7. customThe residue is recrystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-4c1f5c01e3d54deb8e8d18b11778ebad
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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