Hydrochloric Acid → 1,4Benzodiazepine-1-carboxamide

HRID 1605029Notes

Reaction equation

HRID 1605029 reaction equation
C1([C:7]2[C:13]3[CH:14]=[C:15](Cl)[CH:16]=[CH:17][C:12]=3[N:11]3[C:19](C#N)=[N:20]N=[C:10]3[CH2:9][N:8]=2)C=CC=CC=1.Cl.C[OH:26]>[OH-].[Na+]>[N:11]1([C:19]([NH2:20])=[O:26])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:7]=[N:8][CH:9]=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 125624996-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 214860201,4Benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.60 g (0.005 mole) of 6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-carbonitrile in a mixture of 50 ml of methanol and 50 ml of 1N sodium hydroxide solution is allowed to stand for ca. 10 minutes at 25°. The reaction mixture is then neutralised with 2N hydrochloric acid, and concentrated to about half its volume. The concentrate is extracted in methylene chloride, the organic solution washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. The residue is crystallised from methanol/ethyl acetate/petroleum ether to obtain 6-phenyl-8-chloro-4H-s-triazolo [4,3-a][1,4benzodiazepine-1-carboxamide, M.P. 285°-289°.

Workup

  1. concentrationconcentrated to about half its volume
  2. extractionThe concentrate is extracted in methylene chloride
  3. washthe organic solution washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe residue is crystallised from methanol/ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-5458ea1c16b64011bbe67d6a2a46d47d
Source dataset
uspto-grants-1976_04
Patent number
US03948931

Reaction notes

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