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

HRID 973913Notes

Reaction equation

HRID 973913 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>O.O1CCCC1>[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 100 ml of tetrahydrofuran solution containing 6.6 g (0.1 mol) of malononitrile was added 4.0 g (0.1 mol) of 60 wt % sodium hydride under cooling with ice, then 17 g (0.1 mol) of 6-chloro-1,3-dimethyluracil was added thereto and the mixture was stirred for 5 hours at room temperature. The reaction mixture was mixed with 100 ml of water, neutralized with concentrated hydrochloric acid, and thereafter extracted with 200 ml of ethyl acetate. The extract was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the crystals thus-deposited were collected by filtration to obtain 12.9 g (63%) of 6-dicyanomethyl-1,3-dimethyluracil.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with 200 ml of ethyl acetate
  3. dry with materialThe extract was dried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. filtrationthe crystals thus-deposited were collected by filtration

Sources & evidence

ORD record
ord-f76ec6656bf349269ccec7bb2afdb693
Source dataset
uspto-grants-1991_11
Patent number
US05066573

Reaction notes

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