2-Methylimidazole → 2-(alpha-aminoethylidene) hydrazino-7-chloro-5-phenyl-3H-1,4-benzodiazepine

HRID 1764519Notes

Reaction equation

HRID 1764519 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.[C:22](N)(=[NH:24])[CH3:23].CC1NC=CN=1>C(Cl)(Cl)Cl>[NH2:24][C:22](=[N:13][NH:12][C:10]1[CH2:9][N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[CH:20]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]=1)[CH3:23]

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 67170Acetamidine monohydrochlorideHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 706273862-(alpha-aminoethylidene) hydrazino-7-chloro-5-phenyl-3H-1,4-benzodiazepine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2.8 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine, 2.8 parts of acetamidine hydrochloride, 2.5 parts of 2-methylimidazole and 100 parts by volume of chloroform is stirred at room temperature for 24 hours. The chloroform layer is washed with water, dried over sodium sulfate and the solvent is evaporated. After treating the residue with diethyl ether, the resulting crystals are subjected to extraction with hot methanol. Evaporation of the methanol gives 2-(α-aminoethylidene) hydrazino-7-chloro-5-phenyl-3H-1,4-benzodiazepine as crystals. Recrystallization from acetone yields pale yellow needles melting at 203° C to 205° C (effervescence).

Workup

  1. washThe chloroform layer is washed with water
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated
  4. additionAfter treating the residue with diethyl ether
  5. extractionthe resulting crystals are subjected to extraction with hot methanol
  6. customEvaporation of the methanol

Sources & evidence

ORD record
ord-51a9dc3c41724d3594b1a7cd02055857
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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