Dimethyl Sulfate → 1-Methyl-3-(1-methylethyl)-pyrido(2,3-c)(1,2,6)-thiadiazin-4(3H)-one-2,2-dioxide

HRID 65814Notes

Reaction equation

HRID 65814 reaction equation
[CH3:1][CH:2]([N:4]1[S:9](=[O:11])(=[O:10])[NH:8][C:7]2[N:12]=[CH:13][CH:14]=[CH:15][C:6]=2[C:5]1=[O:16])[CH3:3].[H-].[Na+].S(OC)(O[CH3:23])(=O)=O>COCCOCCOC>[CH3:23][N:8]1[C:7]2[N:12]=[CH:13][CH:14]=[CH:15][C:6]=2[C:5](=[O:16])[N:4]([CH:2]([CH3:1])[CH3:3])[S:9]1(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 136092433-(1-Methylethyl)pyrido(2,3-c) (1,2,6)thiadiazin-4(3H)-one-2,2-dioxide

Product 1

HCID 227567831-Methyl-3-(1-methylethyl)-pyrido(2,3-c)(1,2,6)-thiadiazin-4(3H)-one-2,2-dioxide

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

3-(1-Methylethyl)pyrido(2,3-c)(1,2,6)thiadiazin-4(3H)-one-2,2-dioxide (5.0 grams; 0.0208 mole) was mixed with 50 ml of diethylene glycol dimethyl ether. The system was flushed with nitrogen and sodium hydride (1.0 gram; 0.02 mole), previously washed with n-hexane, was added portionwise to the reaction mixture. After the effervescence of hydrogen ceased, 2.2 ml of dimethyl sulfate (0.023 mole, 1.33 g/ml) was added and the reaction mixture heated at reflux temperatures for a period of 4 hours. During the reaction, the color of the reaction mixture changed from light yellow to deep red and gradually back to yellow.

Workup

  1. washpreviously washed with n-hexane
  2. additionwas added portionwise to the reaction mixture
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux temperatures for a period of 4 hours
  5. customDuring the reaction

Sources & evidence

ORD record
ord-93531b3f958944f593896806d9f8c7b0
Source dataset
uspto-grants-1978_12
Patent number
US04128551

Reaction notes

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