Hydrazine hydrate (1:1) → 3-Cyanoamino-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine

HRID 2290375Notes

Reaction equation

HRID 2290375 reaction equation
O.[NH2:2][NH2:3].[C:4]([N:6]=[C:7](SC)[NH:8][CH:9]([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)#[N:5].C[O-].[Na+]>CO>[C:4]([NH:6][C:7]1[NH:2][N:3]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]([CH3:18])[N:8]=1)#[N:5]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 10942334Sodium MethoxideHCID 178503917HCID 178503917, compound

Product 1

HCID 155863703-Cyanoamino-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazineYield 50.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine hydrate (4.55 g) was added to a solution of 2-(3-cyano-2-methyl-1-isothioureido)propiophenone (5.43 g) in methanol (20 ml), and the mixture was allowed to stand at room temperature for 1 hour. After addition of catalytic amount of sodium methoxide to the solution, the mixture was allowed to stand at room temperature for 2 hours with occasional shaking. The resultant preapitates were collected, washed successively with methanol, water and methanol and dried. Thus obtained product was dissolved with dimethylformamide (25 ml), the solution was filtered by suction and then water (25 ml) was added thereto little by little. After cooling, the resultant precipitates were collected by filtration, washed successively with ethanol, water and ethanol, and dried to give 3-cyanoamino-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine (2.37 g), m.p. 244.5°~245° C. (decomp.).

Workup

  1. waitto stand at room temperature for 2 hours with occasional shaking
  2. customThe resultant preapitates were collected
  3. washwashed successively with methanol, water and methanol
  4. customdried
  5. dissolutionThus obtained product was dissolved with dimethylformamide (25 ml)
  6. filtrationthe solution was filtered by suction
  7. additionwater (25 ml) was added
  8. temperatureAfter cooling
  9. customthe resultant precipitates
  10. filtrationwere collected by filtration
  11. washwashed successively with ethanol, water and ethanol
  12. customdried

Sources & evidence

ORD record
ord-dda8f2c12e244b7caf0bffeadaa87006
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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