Water → HCID 12323798, compound

HRID 1284040Notes

Reaction equation

HRID 1284040 reaction equation
O.[NH2:2][NH2:3].[C:4]1([C:10]([C:17]([O:19]CC)=O)=[N:11][N:12]=[C:13](Cl)[CH2:14][CH3:15])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CN(C)C=O>[CH2:14]([C:13]1[N:2]([NH2:3])[C:17](=[O:19])[C:10]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][N:12]=1)[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 53999764HCID 53999764, compound

Product 1

HCID 12323798HCID 12323798, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10.0 g (0.2 mol) of hydrazine hydrate, dissolved in 20 ml of dimethylformamide, were added dropwise to a solution of 26.7 g (0.1 mol) of 1-phenyl-1-ethoxycarbonyl-4-chloro-4-ethyl-2,3-diazabutadiene in 100 ml of dimethylformamide at a temperature of 5°C to 10°C, whilst stirring. After stirring for 3 hours, 250 ml of water were added to the reaction mixture. The whole was left to stand overnight. Thereafter, the solid which had precipitated was filtered off, well rinsed with water and dried. The yellowish-white crude product (17.4 g = 80% of theory) was purified by recrystallization from isopropanol/water. 14.5 g (67.1% of theory) of 3-ethyl-4-amino-6-phenyl-5-H-1,2,4-triazin-5-one of melting point 164°C were obtained.

Workup

  1. stirringAfter stirring for 3 hours
  2. waitThe whole was left
  3. customThereafter, the solid which had precipitated
  4. filtrationwas filtered off
  5. washwell rinsed with water
  6. customdried
  7. customThe yellowish-white crude product (17.4 g = 80% of theory) was purified by recrystallization from isopropanol/water

Sources & evidence

ORD record
ord-04811fb527114872af7f443ad86d7993
Source dataset
uspto-grants-1976_08
Patent number
US03978068

Reaction notes

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