Hydrochloric Acid → Aminotriazinone 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine

HRID 439582Notes

Reaction equation

HRID 439582 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.[NH2:15][N:16]1[CH2:21][C:20](C)=[N:19]NC1=O.[CH3:24][OH:25]>>[NH2:9][N:4]1[CH2:3][C:2]([CH3:1])=[N:7][NH:6][C:5]1=[O:8].[NH2:15][C:16]1[C:24](=[O:25])[NH:4][N:19]=[N:20][CH:21]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 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 67620103Aminotriazinone 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazineYield 99.2%

Conditions

Temperature
45 °C

Procedure

A suspension is prepared of 39.9 g (0.234 mol) 6-methyl-4-acetylamino-4,5-dihydro-1,2,4-triazin-3-(2H)-one in 99 g 95% methanol. The suspension is heated to 45° C. and becomes a clear colourless solution. At between 45° and 50° C. a total of 15.4 g (0.421 mol) HCl are bubbled through this solution over a 2 to 3 hour period. After about 30% of the HCl 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 of over 99% is reached. The reaction mixture is brought to pH 5 by the addition of 50% NaOH solution. The free aminotriazinone 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine is formed in an amount of 29.7 g representing 14.3% by weight of the solution. This represents a yield of 99.2% of theory.

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-b90b127a81b84606b8f5f20ca14982d1
Source dataset
uspto-grants-1996_05
Patent number
US05514795

Reaction notes

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