p-Toluenesulfonic acid → 1,3,5-Triazine-2,4(1H,3H)-dione, 1-amino-3-(2,2-dimethylpropyl)-6-(ethylthio)-

HRID 1248467Notes

Reaction equation

HRID 1248467 reaction equation
C(=[N:8][N:9]1[C:14]([S:15][CH2:16][CH3:17])=[N:13][C:12](=[O:18])[N:11]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]1=[O:24])C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[NH2:8][N:9]1[C:14]([S:15][CH2:16][CH3:17])=[N:13][C:12](=[O:18])[N:11]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]1=[O:24]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 54115501HCID 54115501, compound

Product 1

HCID 1569011,3,5-Triazine-2,4(1H,3H)-dione, 1-amino-3-(2,2-dimethylpropyl)-6-(ethylthio)-Yield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

5.2 g (0.015 mol) of 1-benzylideneamino-6-ethylthio-3-neopentyl-1,3,5-triazine-2,4(1H,3H)-dione (V-1), 3 g (0.015 mol) of S-ethyl-isothiosemicarbazide hydrobromide (VI-1, X=Br) and a spatula-tip of p-toluenesulphonic acid in 80 ml of toluene are stirred at 50°-55° C. for 12 hours. After the mixture has cooled, 0.6 g (0.015 mol) of sodium hydroxide in 5.4 g of water is added dropwise and the mixture is stirred at room temperature for 1 hour. The solid which has precipitated is filtered off and dried. 3.75 g (=95% of theory) of 1-amino-6-ethylthio-3-neopentyl-1,3,5-triazine-2,4(1H,3H)-dione (I-1) of melting point 204°-205° C. are obtained.

Workup

  1. temperatureAfter the mixture has cooled
  2. customThe solid which has precipitated
  3. filtrationis filtered off
  4. customdried

Sources & evidence

ORD record
ord-537f970fa6864afca186488ec4c87a80
Source dataset
uspto-grants-1985_06
Patent number
US04524205

Reaction notes

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