Hydrazine hydrate (1:1) → HCID 57236670, compound

HRID 2399150Notes

Reaction equation

HRID 2399150 reaction equation
O.NN.[CH2:4]([N:6]([CH2:41][CH3:42])[C:7]([C:9]1[N:13]=[C:12]([CH2:14][N:15]2[C:19](=O)[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3C2=O)[N:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2C(=O)C2C=CC=CC=2)[N:10]=1)=[O:8])[CH3:5]>C(O)C>[CH2:4]([N:6]([CH2:41][CH3:42])[C:7]([C:9]1[N:13]=[C:12]2[CH2:14][N:15]=[C:19]([C:18]3[CH:17]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:31]3[CH:30]=[C:29]([Cl:32])[CH:28]=[CH:27][C:26]=3[N:11]2[N:10]=1)=[O:8])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20309868HCID 20309868, compound

Product 1

HCID 57236670HCID 57236670, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 105 g (0.021 mole) of hydrazine hydrate is added to a solution of 5.41 g (0.01 mole) of N,N-diethyl-1-(2-benzoyl-4-chlorophenyl)-5-(phthalimidomethyl)-1H-1,2,4-triazole-3-carboxamide in 150 ml of ethanol, and the reaction mixture stirred for 16 hours at room temperature and for a further 5 hours at 60°. The formed phthalic acid hydrazide is then filtered off, and the filtrate concentrated in vacuo to dryness. Ice water is added to the residue, and extraction performed twice with ethyl acetate. The organic phase is washed twice with ice cold 1N sodium hydroxide solution, once with ice cold 1N hydrochloride acid solution, and twice with water. After drying of the solution over sodium sulphate, the solvent is evaporated off in vacuo. After recrystallisation from benzene/cyclohexane, the residue yields N,N-diethyl-6-phenyl-8-chloro-4H-s-triazolo[1,5-a] [1,4]benzodiazepine-2-carboxamide, M.P. 175°-177°.

Workup

  1. filtrationThe formed phthalic acid hydrazide is then filtered off
  2. concentrationthe filtrate concentrated in vacuo to dryness
  3. additionIce water is added to the residue, and extraction
  4. washThe organic phase is washed twice with ice cold 1N sodium hydroxide solution, once with ice cold 1N hydrochloride acid solution
  5. dry with materialAfter drying of the solution over sodium sulphate
  6. customthe solvent is evaporated off in vacuo
  7. customAfter recrystallisation from benzene/cyclohexane

Sources & evidence

ORD record
ord-6be640ba7dc94916af8373950206bb3d
Source dataset
uspto-grants-1977_05
Patent number
US04027029

Reaction notes

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