Toluene → 3-Cyclohexyl-1-methyl-6-(methylsulfanyl)-1,3,5-triazine-2,4(1H,3H)-dione

HRID 1576766Notes

Reaction equation

HRID 1576766 reaction equation
[C:1]1(C)C=CC=CC=1.[Na].[CH:9]1([N:15]2[C:20](=[O:21])[N:19]=[C:18]([S:22][CH3:23])[NH:17][C:16]2=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.S(OC)(OC)(=O)=O.[OH-].[Na+]>O>[CH3:1][N:19]1[C:18]([S:22][CH3:23])=[N:17][C:16](=[O:24])[N:15]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[C:20]1=[O:21]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 68140575HCID 68140575, compound

Product 1

HCID 132960803-Cyclohexyl-1-methyl-6-(methylsulfanyl)-1,3,5-triazine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This toluene slurry of 3-cyclohexyl-6-methylthio-s-triazine-2,4(1H,3H)-dione sodium salt is then agitated with 650 parts of water for 0.15 hrs. The aqueous layer is separated and reacted at 25°-30° during 0.25 hrs with 57 parts of dimethyl sulfate. After the dimethyl sulfate is added, the pH of the reaction is maintained at pH 9-9.5 by addition of a total of 7.5 parts of 50% aqueous sodium hydroxide. The total reaction time is 1.8 hrs at which time filtration and drying gives 70 parts of white 1-methyl-3-cyclohexyl-6-methylthio-s-triazine-2,4(1H,3H)-dione, m.p. 137°-139°.

Workup

  1. customThe aqueous layer is separated
  2. customreacted at 25°-30° during 0.25 hrs with 57 parts of dimethyl sulfate
  3. filtrationThe total reaction time is 1.8 hrs at which time filtration
  4. customdrying

Sources & evidence

ORD record
ord-5e079b8e17454ae89145a716a27858da
Source dataset
uspto-grants-1976_09
Patent number
US03983116

Reaction notes

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