Acetic Anhydride → 6-Amino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1758917Notes

Reaction equation

HRID 1758917 reaction equation
[C:1](CC(O)=O)#[N:2].[CH2:7]([NH:9][C:10]([NH2:12])=[O:11])[CH3:8].C(O[C:17](=[O:19])[CH3:18])(=O)C>>[NH2:2][C:1]1[N:9]([CH2:7][CH3:8])[C:10](=[O:11])[NH:12][C:17](=[O:19])[CH:18]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 12254Ethylurea

Product 1

HCID 8538996-Amino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Procedure

To a solution of 127.5 g (1.5 mol) cyanoacetic acid and 200 ml of acetic anhydride was added 120 g (1.36 mol) of ethylurea. The solution was stirred at 60°-70° C. for 2 hours. After cooling, white crystals were filtered off and washed with ethanol. Yield 153 g (74%) (I). This was stirred in 1 liter of hot water and 160 ml of 2 N NaOH was added in portions so the solution the whole time was basic. The reaction mixture was refluxed for 20 minutes and then neutralized with 5 N HCl. After cooling, white crystals were filtered off. Yield 100 g (65%) (II) NMR.

Workup

  1. temperatureAfter cooling
  2. filtrationwhite crystals were filtered off
  3. washwashed with ethanol
  4. stirringThis was stirred in 1 liter of hot water
  5. addition160 ml of 2 N NaOH was added in portions so the solution the whole time
  6. temperatureThe reaction mixture was refluxed for 20 minutes
  7. temperatureAfter cooling
  8. filtrationwhite crystals were filtered off

Sources & evidence

ORD record
ord-03f980486b5944cdaf5d2a3bf9624134
Source dataset
uspto-grants-1982_07
Patent number
US04338319

Reaction notes

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