Dimethyl Sulfate → HCID 20291420, compound

HRID 1413308Notes

Reaction equation

HRID 1413308 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]2[C:10]=1[CH:9]=[N:8][NH:7][C:6]2=[S:11].S(OC)(O[CH3:22])(=O)=O>C(=O)(O)[O-].[Na+]>[CH3:22][N:7]1[C:6](=[S:11])[N:5]2[C:4]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[N:3][C:2]([CH3:1])=[C:10]2[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 13548752HCID 13548752, compound

Product 1

HCID 20291420HCID 20291420, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

8-Methyl-6-phenyl-imidazo[1,5-d]-as-triazin-4(3H)-thione (3.76 g, 0.014 mole) is dissolved in aqueous sodium bicarbonate (125 ml. 6.7%). Dimethyl sulfate (1.85 g, 0.0147 mole) is added at room temperature and the reaction mixture stirred overnight (appr. 15-16 hours). The precipitated solid is collected by filtration and washed thoroughly with water. The dried solid (3.84 g) is extracted with benzene. The benzene solution is evaporated to dryness, and the residual red solid obtained is extracted with hexane. Evaporation of the hexane solution yields a tan solid (0.25 g). Recrystallization of this tan solid from methanol yields pale yellow crystals, m.p. 194°-195° C.

Workup

  1. filtrationThe precipitated solid is collected by filtration
  2. washwashed thoroughly with water
  3. extractionThe dried solid (3.84 g) is extracted with benzene
  4. customThe benzene solution is evaporated to dryness
  5. customthe residual red solid obtained
  6. extractionis extracted with hexane
  7. customEvaporation of the hexane solution

Sources & evidence

ORD record
ord-daa5c29581764a3a92ed2fd132902862
Source dataset
uspto-grants-1981_02
Patent number
USRE030511

Reaction notes

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