Hydrazine hydrate (1:1) → HCID 15586387, compound

HRID 2290373Notes

Reaction equation

HRID 2290373 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([NH:11][C:12]([O:14]CC)=O)[CH3:10])=[CH:4][CH:3]=1.O.[NH2:19][NH2:20]>C(O)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:10])[NH:11][C:12](=[O:14])[NH:19][N:20]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15586412HCID 15586412, compound

Product 1

HCID 15586387HCID 15586387, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4'-bromo-2-ethoxycarbonylaminopropiophenone (4.29 g), hydrazine hydrate (8 g) and n-butanol (50 ml) was refluxed under heating for 68 hours. The solution was evaporated to dryness, and the resultant residue was dissolved in a mixture of chloroform and methanol. The solution was washed with water and the washings were extracted with chloroform. The combined organic layer was dried over magnesium sulfate and evaporated to dryness. The resultant residue was washed with diisopropyl ether and recrystallized from ethanol to give colorless crystals of 6-(4-bromophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.68 g), m.p. 213.5°~215° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 68 hours
  3. customThe solution was evaporated to dryness
  4. dissolutionthe resultant residue was dissolved in a mixture of chloroform and methanol
  5. washThe solution was washed with water
  6. extractionthe washings were extracted with chloroform
  7. dry with materialThe combined organic layer was dried over magnesium sulfate
  8. customevaporated to dryness
  9. washThe resultant residue was washed with diisopropyl ether
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-84ca2d6aef574b6aa1eef6dd058efb12
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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