7-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine → HCID 53749252, compound

HRID 328386Notes

Reaction equation

HRID 328386 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]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.Cl.[CH2:22]([N:24]([CH2:33][CH3:34])[CH2:25][CH2:26][CH2:27][C:28](=O)[C:29]([OH:31])=[O:30])[CH3:23]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[C:28]([C:29]([OH:31])=[O:30])[CH2:27][CH2:26][CH2:25][N:24]([CH2:33][CH3:34])[CH2:22][CH3:23])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepineHCID 131710708HCID 131710708, compound

Product 1

HCID 53749252HCID 53749252, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2.85 g. (0.01 mole) of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in 100 ml. of methanol is added 2.24 g. (0.01 mole) of 5-(diethylamino)-2-oxo-valeric acid, hydrochloride [prepared by the method of Libman and Kutznetsov J. Gen. Chem. (USSR), 33, 1938 (1963)]. The mixture is kept under nitrogen at ambient temperature for 2 hours and then concentrated in vacuo. The residue is mixed with aqueous sodium bicarbonate and extracted with methylene chloride. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue of 7-chloro-2-[[1-carboxy-4-(diethylamino)-butylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine is used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is mixed with aqueous sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue of 7-chloro-2-[[1-carboxy-4-(diethylamino)-butylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine is used without further purification

Sources & evidence

ORD record
ord-6c64648af2104185bb082a2f0ef3b944
Source dataset
uspto-grants-1977_04
Patent number
US04017492

Reaction notes

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