Pyridine → HCID 13386049, compound

HRID 2290733Notes

Reaction equation

HRID 2290733 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][N:17]=[C:18]=[O:19].N1C=CC=CC=1>C(O)C>[CH3:16][NH:17][C:18](=[O:19])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12228Methyl IsocyanateHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13386049HCID 13386049, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.5 g), methyl isocyanate (0.48 ml) and pyridine (40 ml) was stirred at room temperature for 4.5 hours, and ethanol (5 ml) was added. The solvent was then distilled off under reduced pressure. To the oily residue was added 10% HCl, and the thus-produced crystals were collected by filtration, washed with water, dried and recrystallized from aqueous dimethylformamide to give 6-[4-(3-methylureido)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.43 g).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. additionTo the oily residue was added 10% HCl
  3. filtrationthe thus-produced crystals were collected by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-b30f6ddf7a374bd38bc4835b0c68f988
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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