2-Methoxyacetohydrazide → 1-(methoxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 2296060Notes

Reaction equation

HRID 2296060 reaction equation
CS[C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]=1.[CH3:21][O:22][CH2:23][C:24]([NH:26][NH2:27])=O>CN(C)P(=O)(N(C)C)N(C)C>[CH3:21][O:22][CH2:23][C:24]1[N:4]2[C:5]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:6]=3[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:8][CH2:9][C:3]2=[N:27][N:26]=1

Participants

4

Reactant 2

HCID 27595322-MethoxyacetohydrazideHCID 125708587-chloro-2-methylmercapto-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 125606141-(methoxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 10.0 g of 2-(methylthio)-5-phenyl-7-chloro-3H-1,4-benzodiazepine and 4.85 g of 2-methoxyacetic acid hydrazide (cp. E. J. Browne and J. B. Polya, J.Chem.Soc. 1962, 5149-5152) in 70 ml of abs. hexamethylphosphoric acid triamide is heaated for 11 hours at 140°. The solvent is then distilled off in vacuo. The residue is taken up in methylene chloride; the solution is washed with water and then with saturated sodium chloride solution, dried over sodium sulphate, and concentrated by evaporation. Crystallisation of the concentration residue from ethyl acetate/petroleum ether yields 1-(methoxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine, M.P. 185°-191°. After chromatography of the mother liquor on 100 g of silica gel "Merck", a further amount of final product of the same melting point can be isolated.

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. washthe solution is washed with water
  3. dry with materialwith saturated sodium chloride solution, dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customCrystallisation of the concentration residue from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7cf8edc254f34e37a1f26cc9a614afc5
Source dataset
uspto-grants-1984_01
Patent number
US04427590

Reaction notes

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