2,2-Diethoxyacetohydrazide → 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde-diethylacetal

HRID 268028Notes

Reaction equation

HRID 268028 reaction equation
CS[C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:6]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:5]=2[N:4]=1.[CH2:22]([O:24][CH:25]([O:30][CH2:31][CH3:32])[C:26]([NH:28][NH2:29])=O)[CH3:23]>CN(C)P(=O)(N(C)C)N(C)C>[CH2:22]([O:24][CH:25]([O:30][CH2:31][CH3:32])[C:26]1[N:4]2[C:5]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:6]=3[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])=[N:8][CH2:9][C:3]2=[N:29][N:28]=1)[CH3:23]

Participants

4

Reactant 2

HCID 108557862,2-DiethoxyacetohydrazideHCID 154992837-chloro-5-(2-fluorophenyl)-2-methylthio-3H-1,4-benzodiazepine

Product 1

HCID 215531106-(o-fluorophenyl)-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde-diethylacetal

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 15.9 g of 2-(methylthio)-5-(o-fluorophenyl)-7-chloro-3H-1,4-benzodiazepine and 9.7 g of diethoxyacetic acid hydrazide in 100 ml of hexamethylphosphoric acid triamide is heated for 10 hours at 140°; processing is then carried out analogously to the procedure described in Example 1, and the residue recrystallised from ethyl acetate/petroleum ether to obtain 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carboxaldehyde-diethylacetal, M.P. 120°-121°.

Workup

  1. customthe residue recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-068905ecf3324a1f98ad5ecd2efd92ab
Source dataset
uspto-grants-1976_03
Patent number
US03946032

Reaction notes

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