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

HRID 1576767Notes

Reaction equation

HRID 1576767 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH:11]1([N:17]=[C:18]=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[OH-].[Na+].Cl[C:23](OC)=[O:24].[C:27]1(C)C=CC=CC=1>O>[CH3:27][N:9]1[C:8]([S:7][CH3:6])=[N:10][C:23](=[O:24])[N:17]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:18]1=[O:19]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide2×HCID 18502Cyclohexyl isocyanateHCID 752702-Methyl-2-thiopseudourea sulfate

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

To a solution of 70 parts of 2-methyl-2-thiopseudourea sulfate in 375 parts of water and 400 parts of toluene at 10° is added over 1 hour 62.5 parts of cyclohexyl isocyanate. The pH is maintained at 8.5 by addition of 80 parts of 50% aqueous sodium hydroxide over 1-1.5 hours. The two-phase system is then reacted with 99 parts of methyl chloroformate and 84 parts of 50% aqueous sodium hydroxide during 1 hour. The temperature is maintained at 25°-30°. After the addition is complete the reaction is stirred at 25°-28° for an additional 3 hours. The toluene layer is separated and treated as in Example 5A to give 76 parts of 1-methyl-3-cyclohexyl-6-methylthio-s-triazine-2,4-(1H,3H)-dione, m.p. 136°-138°.

Workup

  1. temperatureThe temperature is maintained at 25°-30°
  2. additionAfter the addition
  3. customThe toluene layer is separated
  4. additiontreated as in Example 5A

Sources & evidence

ORD record
ord-7036fdd6ef8e477694d855d38f90e4c6
Source dataset
uspto-grants-1976_09
Patent number
US03983116

Reaction notes

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