Triethylamine → 1-methyl-8-chloro-6-phenyl-4H-s-triazolo-[4,3-a][1,5]benzodiazepin-5-one

HRID 1763241Notes

Reaction equation

HRID 1763241 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([NH:18]CN=O)[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[C:24]([NH:27]N)(=O)[CH3:25].C(N(CC)CC)C>C(O)CCC>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]3[C:24]([CH3:25])=[N:27][N:18]=[C:7]3[CH2:8][C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14039AcetohydrazideHCID 1785263748-chloro-4-(nitrosomethylamino)-1-phenyl-3H-1,5-benzodiazepin-2-one

Product 1

HCID 122643201-methyl-8-chloro-6-phenyl-4H-s-triazolo-[4,3-a][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.3g (0.01M) of 7-chloro-3,5-dihydro-2-(N-nitrosomethylamino)-5-phenyl-4H-1,5-benzodiazepin-4-one, 2g of acetylhydrazine, 5 ml of triethylamine and 50 ml of n-butanol was heated to reflux for 3 hrs. Half of the solvent was then removed by distillation and replaced by fresh n-butanol. Refluxing was continued for 3 days. The residue obtained after evaporation was chromotographed over 100 g of silical gel(Merck 70-230 mesh) using 10% (v/v) ethanol in methylene chloride for elution. Crystallization of the pure fraction from methylene chloride/ether yielded the above maned product, m.p. 298°-300°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hrs
  3. customHalf of the solvent was then removed by distillation
  4. temperatureRefluxing
  5. customThe residue obtained
  6. customafter evaporation
  7. washfor elution
  8. customCrystallization of the pure fraction from methylene chloride/ether
  9. customyielded the above maned product, m.p. 298°-300°

Sources & evidence

ORD record
ord-cf914d0c7eb64b56a2c3e991d562956b
Source dataset
uspto-grants-1978_09
Patent number
US04111934

Reaction notes

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