Potassium Carbonate → 2-(2-dimethylaminobenzyl)thio-4(3H)-pyrimidinone

HRID 2247856Notes

Reaction equation

HRID 2247856 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[OH-].[Na+].[Cl-].Cl[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH+:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH3:21][N:20]([CH3:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][S:3][C:2]1[NH:4][C:5](=[O:6])[CH:7]=[CH:8][N:1]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 1269845ThiouracilHCID 178486212HCID 178486212, compound

Product 1

HCID 198160832-(2-dimethylaminobenzyl)thio-4(3H)-pyrimidinoneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of 0.38 g (3.0 mmol) of 2-thiouracil [Am. Chem. J. 40, 550 (1908)] in 6 ml of aqueous 1N sodium hydroxide solution is added to the solution of 0.62 g (3.0 mmol) of (2-chloromethylphenyl)dimethylammonium chloride in 6 ml of chloroform at room temperature under vigorous stirring within about 30 minutes. After termination of the addition the pH value of the aqueous solution is controlled and, when necessary, it is adjusted to 9 by adding 20% potassium carbonate solution. Thereafter, the reaction mixture is stirred for 2 hours, the phases are separated, the aqoeous layer is extracted twice with 5 ml of chloroform each, the combined organic phase is washed with 5 ml of 1N sodium hydroxide solution and then twice with 5 ml of water each, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue is thoroughly triturated with petroleum ether, filtered and recrystallized from ethanol to give 0.66 g (84%) of the title compound as a white crystalline product, m.p.: 156°-158° C.

Workup

  1. additionAfter termination of the addition the pH value of the aqueous solution
  2. stirringThereafter, the reaction mixture is stirred for 2 hours
  3. customthe phases are separated
  4. extractionthe aqoeous layer is extracted twice with 5 ml of chloroform each, the combined organic phase
  5. washis washed with 5 ml of 1N sodium hydroxide solution
  6. dry with materialtwice with 5 ml of water each, dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is thoroughly triturated with petroleum ether
  9. filtrationfiltered
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d6baef30ac074eefaadba5ca1abfa9c8
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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