Propionylhydrazine → 8-chloro-1-ethyl-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

HRID 1288049Notes

Reaction equation

HRID 1288049 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[C:20]([NH:24][NH2:25])(=O)[CH2:21][CH3:22]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:20]([CH2:21][CH3:22])=[N:24][N:25]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 79890PropionylhydrazineHCID 826706Thionordiazepam

Product 1

HCID 125606218-chloro-1-ethyl-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
250 °C

Procedure

In the manner given in Example 2, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione was heated in ethanol with propionic acid hydrazide and the resulting product heated to 250° C. to give 8-chloro-1-ethyl-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepine of melting point 231.5°-232.5° C. The ultraviolet spectrum (ethanol) had end absorption λ max. 224 (ε = 39,250) and inflections 248 (ε = 15,000), 266 (ε = 6,900) and 290 mμ(ε = 3,250).

Sources & evidence

ORD record
ord-0efef8f44f6a4cdabdc4419e0f9ad122
Source dataset
uspto-grants-1976_10
Patent number
US03987052

Reaction notes

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