p-Toluenesulfonic acid → 4H-(1,2,4)Triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-1-methyl-6-phenyl-, 5-oxide

HRID 918254Notes

Reaction equation

HRID 918254 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N+:8]([O-:14])=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1.[CH2:22](C(CC)(CC)C([O-])([O-])[O-])[CH3:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:22]([CH3:23])=[N:13][N:12]=[C:10]3[CH2:9][N+:8]([O-:14])=[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21875354TriethylorthoaceateHCID 178514336HCID 178514336, compound

Product 1

HCID 3275544H-(1,2,4)Triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-1-methyl-6-phenyl-, 5-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.5 g. of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine 4-oxide, 200 ml. of ethanol, 9 ml. of triethylorthoacetate and 0.5 g. of p-toluenesulfonic acid was refluxed for 20 minutes. The ethanol was removed under reduced pressure. The residue was partitioned between methylene chloride and aqueous sodium carbonate solution. The methylene chloride layer was dried and evaporated. The remaining crystals were recrystallized from ethyl acetate to yield 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine 5-oxide with a melting point of 280°-282°.

Workup

  1. additionA mixture of 13.5 g
  2. customThe ethanol was removed under reduced pressure
  3. customThe residue was partitioned between methylene chloride and aqueous sodium carbonate solution
  4. dry with materialThe methylene chloride layer was dried
  5. customevaporated
  6. customThe remaining crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8fc909018a2d4b5a84358046e782d124
Source dataset
uspto-grants-1976_07
Patent number
US03970664

Reaction notes

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