Dimethylamine → Hexazinone

HRID 1576768Notes

Reaction equation

HRID 1576768 reaction equation
[CH3:1][N:2]1[C:7](SC)=[N:6][C:5](=[O:10])[N:4]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]1=[O:17].[CH3:18][NH:19][CH3:20]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:7]([N:19]([CH3:20])[CH3:18])=[N:6][C:5](=[O:10])[N:4]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]1=[O:17]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 132960803-Cyclohexyl-1-methyl-6-(methylsulfanyl)-1,3,5-triazine-2,4(1H,3H)-dione

Product 1

HCID 39965Hexazinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 300 parts of 1-methyl-3-cyclohexyl-6-methylthio-s-triazine-2,4(1H,3H)-dione in 887 parts of toluene is stirred at 25°-30° for three hours with 150 parts of dimethylamine. Toluene is distilled from the reaction until a pot temperature of 125° is attained. The reaction mass is cooled to 50° at which time 480 parts of hexane is added over 0.66 hours. The slurry at 25° is filtered to give 282 parts of crystalline 1-methyl-3-cyclohexyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, m.p. 110°-115°.

Workup

  1. distillationToluene is distilled from the reaction until a pot temperature of 125°
  2. temperatureThe reaction mass is cooled to 50° at which time 480 parts of hexane
  3. additionis added over 0.66 hours
  4. filtrationThe slurry at 25° is filtered

Sources & evidence

ORD record
ord-bf3c393e45574de496b123cc50993fb7
Source dataset
uspto-grants-1976_09
Patent number
US03983116

Reaction notes

Loading…