Hydrochloric Acid → 6-Dicyanomethyl-1,3-dimethyluracil

HRID 648889Notes

Reaction equation

HRID 648889 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].Cl[C:9]1[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[O:18])[CH:10]=1.Cl>O1CCCC1.O>[C:3]([CH:2]([C:1]#[N:5])[C:9]1[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[O:18])[CH:10]=1)#[N:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 24758Sodium hydrideHCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 136847646-Dicyanomethyl-1,3-dimethyluracilYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.6 g (0.1 mol) of malononitrile in 100 ml of tetrahydrofuran was added 4.0 g (0.1 mol) of 60 wt% sodium hydride under ice-cooling. Seventeen grams (0.1 mol) of 6-chloro-1,3-dimethyluracil were added thereto, followed by stirring at room temperature for 5 hours. A hundred milliliters of water were added to the mixture, and the mixture was neutralized with concentrated hydrochloric acid, followed by extraction with 200 ml of ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, followed by filtration to obtain 12.9 g (63%) of 6-dicyanomethyl-1,3-dimethyluracil.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with 200 ml of ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-c625dde784e8470fa98570c0a6a3f616
Source dataset
uspto-grants-1988_04
Patent number
US04737442

Reaction notes

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