Hydrochloric Acid → 3-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine

HRID 2290353Notes

Reaction equation

HRID 2290353 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH2:7][C:8]([NH:10][NH:11][C:12]1[N:13]=[N:14][C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:16]([CH3:18])[N:17]=1)=[O:9])=[O:5])[CH3:2].Cl>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([NH:6][CH2:7][C:8]([NH:10][NH:11][C:12]1[NH:13][N:14]=[C:15]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]([CH3:18])[N:17]=1)=[O:9])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 202320623-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazine

Product 1

HCID 155863603-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazineYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazine (1.815 g) in ethanol (32 ml) containing anhydrous hydrogen chloride was shaken with 5% palladium on carbon (0.4 g) under atmosphere of hydrogen gas at room temperature. After the theoretical amount of hydrogen gas was absorbed, the catalyst was filtered off, and the filtrate was evaporated. The residue was dissolved in water and made alkaline with an aqueous solution of sodium bicarbonate under ice cooling. The resulting precipitates were collected by filtration, washed with water, dried, and recrystallized from ethanol to give colorless crystals of 3-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-2,5-dihydro-1,2,4-triazine (1.198 g), m.p. 144.5°~145.5° C.

Workup

  1. customAfter the theoretical amount of hydrogen gas was absorbed
  2. filtrationthe catalyst was filtered off
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in water
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8b666d62dba345a097b82fecb88d6704
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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