7-chloro-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepine → 1-(fluoromethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 2296063Notes

Reaction equation

HRID 2296063 reaction equation
CS[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]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]=1.[F:21][CH2:22][C:23]([NH:25][NH2:26])=O>CN(C)P(=O)(N(C)C)N(C)C>[F:21][CH2:22][C:23]1[N:4]2[C:5]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:6]=3[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8][CH2:9][C:3]2=[N:26][N:25]=1

Participants

4

Reactant 2

HCID 125708587-chloro-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepineHCID 197891952-Fluoroacetic acid hydrazide

Product 1

HCID 204730741-(fluoromethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 8 g of 2-(methylthio)-5-phenyl-7-chloro-3H-1,4-benzodiazepine and 3.68 g of 2-fluoroacetic acid hydrazide [cp. M. A. Phillips, Agr.Vet.Chem. 2, 86-87 (1961), C. A. 57, 12314 (1962)] in 80 ml of hexamethylphosphoric acid triamide is heated for 8 hours at 140° The solvent is then distilled off in vacuo, and the residue distributed between methylene chloride and water. The organic phase is separated, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, and concentrated by evaporation. The residue is recrystallized from ethyl acetate/petroleum ether to obtain 1-(fluoromethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine, M.P. 153°-154°.

Workup

  1. distillationis then distilled off in vacuo
  2. customThe organic phase is separated
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-fcadbb4a5da643d1a1ed9bbde3d48d36
Source dataset
uspto-grants-1984_01
Patent number
US04427590

Reaction notes

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