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

HRID 265615
Notes
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Reaction equation

HRID 265615 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.C([O-])(=O)C.[Na+]>CO>[NH2:4][N:5]1[CH2:10][C:9]([CH3:11])=[N:8][NH:7][C:6]1=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 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
50 °C

Procedure

A mixture of 85 g of 4-acetylamino-6-methyl-3-oxo-2,3,4,5-tetrahydro- 1,2,4-triazine, 63 ml of hydrochloric acid (37%) and 250 ml of methanol is stirred for 4 hours at 50° C. After cooling to 15° C., 82 g of sodium acetate are added, the mixture is stirred for a further 15 minutes, and the solvent is removed by evaporation. 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 filtered off, the filtrate is evaporated to dryness, the residue is caused to crystallize by adding 50 ml of acetic acid ethyl ester at ambient temperature, and the crystals are filtered off and dried yielding 54.6 g (85% of the theoretical amount) of the title compound having a melting point of 113°-118° C.

Workup

  1. temperatureAfter cooling to 15° C.
  2. stirringthe mixture is stirred for a further 15 minutes
  3. customthe solvent is removed by evaporation
  4. customthe solvent is removed again in vacuo
  5. customundissolved salt precipitates
  6. filtrationare filtered off
  7. customthe filtrate is evaporated to dryness
  8. customto crystallize
  9. additionby adding 50 ml of acetic acid ethyl ester at ambient temperature
  10. filtrationthe crystals are filtered off
  11. customdried

Sources & evidence

ORD record
ord-ad18e7bb6ec042939d38f014dd918ce5
Source dataset
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05648487

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes