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

HRID 439583
Notes
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Reaction equation

HRID 439583 reaction equation
[CH3:1][C:2]1[CH2:3][N:4]([NH:9]C(=O)C)[C:5](=[O:8])[NH:6][N:7]=1.Cl.Cl.NN1CC(C)=NNC1=O>CO>[NH2:9][N:4]1[CH2:3][C:2]([CH3:1])=[N:7][NH:6][C:5]1=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric Acid4×HCID 11008343N-(6-Methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl)acetamideHCID 190369254-Amino-6-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one--hydrogen chloride (1/1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A suspension is prepared of 6-methyl-4-acetylamino-4,5-dihydro-1,2,4-triazin-3-(2H)-one in methanol. The suspension is heated to 45° C. and becomes a clear colourless solution. At between 45° C. and 50° C. gaseous HCl (a) or aqueous HCl (b) is added to this solution over a 2 to 3 hour period. After about 30% of the gaseous HCl (a) or 50% of the aqueous HCl (b) has been added the reaction mixture is seeded with 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride. Thereafter 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine precipitates out continuously as the hydrochloride salt. After about 2 hours stirring, the maximum conversion is reached. The reaction mixture is brought to pH 5 by the addition of 50% NaOH solution, thereby forming free 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Workup

  1. customThereafter 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine precipitates out continuously as the hydrochloride salt
  2. additionThe reaction mixture is brought to pH 5 by the addition of 50% NaOH solution

Sources & evidence

ORD record
ord-16bf86a1adb3445aaf6aaa6aa755a471
Source dataset
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05514795

Reaction notes

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