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

Participants

Reaction Steps

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°.

Provenance & Evidence