p-Toluenesulfonic acid → HCID 21399304, compound

HRID 1438840Notes

Reaction equation

HRID 1438840 reaction equation
[CH3:1][NH2:2].[NH2:3][N:4]1[C:9](=[O:10])[C:8]([CH:11]([CH2:13][CH3:14])[CH3:12])=[N:7][N:6]=[C:5]1SC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[NH2:3][N:4]1[C:9](=[O:10])[C:8]([CH:11]([CH2:13][CH3:14])[CH3:12])=[N:7][N:6]=[C:5]1[NH:2][CH3:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6329MethylamineHCID 23050531HCID 23050531, compound

Product 1

HCID 21399304HCID 21399304, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Monomethylamine was passed for 4 hours into a boiling solution of 42.8 g of 4-amino-6-sec.-butyl-3-methylthio-1,2,4-triazin-5 (4H)-one of which 12 ml of glacial acetic acid and 1 g of p-toluenesulfonic acid had been added, and the mixture was then boiled for a further 4 hours under reflux. The solvent was largely evaporated off in vacuo and the oily residue was taken up in methylene chloride and repeatedly shaken with 10% strength sodium carbonate solution. The organic phase was separated off and concentrated by evaporation. 38.6 g (98% of theory) of 4-amino-6-sec.-butyl-3-methylamino-1,2,4-triazin-5 (4H)-one which gradually solidified, remained. The product was purified further by recrystallization from carbon tetrachloride. Melting point = 117° C.

Workup

  1. additionhad been added
  2. temperatureunder reflux
  3. customThe solvent was largely evaporated off in vacuo
  4. customThe organic phase was separated off
  5. concentrationconcentrated by evaporation
  6. customThe product was purified further by recrystallization from carbon tetrachloride

Sources & evidence

ORD record
ord-8281c43b478c4ec8a0e5fa7032301197
Source dataset
uspto-grants-1977_11
Patent number
US04057417

Reaction notes

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