Hydrochloric Acid → 4-Amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one

HRID 864105Notes

Reaction equation

HRID 864105 reaction equation
C([NH:4][N:5]1[CH2:10][C:9]([CH3:11])=[N:8][NH:7][C:6]1=[O:12])(=O)C.Cl.O.[OH-].[Na+]>CO>[NH2:4][N:5]1[CH2:10][C:9]([CH3:11])=[N:8][NH:7][C:6]1=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 11008343N-(6-Methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl)acetamide

Product 1

HCID 109755004-Amino-6-methyl-2,5-dihydro-1,2,4-triazin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

85 g of 4-acetylamino-6-methyl-3-oxo-2,3,4,5-tetrahydro-l,2,4-triazine in 250 ml of methanol are stirred together with 63 ml of hydrochloric acid (37%) for 4 hours at 50° C. After cooling to 5° C., 250 ml of icecold water and 125 ml of sodium hydroxide solution (50%) are added. The solvent is removed by evaporation in vacuo. The residue is taken up in 100 ml of ethanol, and the solvent is removed again in vacuo. The residue is taken up in 1200 ml of acetonitrile, undissolved salt precipitates are removed by filtration, the filtrate is concentrated to a small volume, the residue is caused to crystallise by adding 100 ml of acetic acid ethyl ester at 0° C., and the colourless crystals are filtered off and dried yielding 60.4 g (92% of the theoretical amount) of the title compound having a melting point of 118°-120° C.

Workup

  1. customThe solvent is removed by evaporation in vacuo
  2. customthe solvent is removed again in vacuo
  3. customundissolved salt precipitates
  4. customare removed by filtration
  5. concentrationthe filtrate is concentrated to a small volume
  6. customto crystallise
  7. additionby adding 100 ml of acetic acid ethyl ester at 0° C.
  8. filtrationthe colourless crystals are filtered off
  9. customdried

Sources & evidence

ORD record
ord-40a9143031e24cdd8013b5f25057c618
Source dataset
uspto-grants-1996_10
Patent number
US05561230

Reaction notes

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