Cyanoacetic acid → 6-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 2285901Notes

Reaction equation

HRID 2285901 reaction equation
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].[CH2:7]([NH:11][C:12]([NH2:14])=[O:13])[CH2:8][CH2:9][CH3:10]>C(OC(=O)C)(=O)C>[NH2:2][C:1]1[N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[C:12](=[O:13])[NH:14][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 11595Butylurea

Product 1

HCID 24289966-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 46 g (0.55 mol) cyanoacetic acid and 100 ml of acetic anhydride was added 58 g (0.5 mol) of n-butylurea. The solution was stirred at 70° C. for 2 hours. After cooling white crystals were filtered off and washed with ethanol. Yield 68 g (74% (VII). This was stirred in 500 ml of water and 20 ml of 5 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 50.6 g (75%) (VIII), NMR.

Workup

  1. temperatureAfter cooling white crystals
  2. filtrationwere filtered off
  3. washwashed with ethanol
  4. stirringThis was stirred in 500 ml of water
  5. addition20 ml of 5 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-2c9bfa3d1d2d4bb283612e980e337774
Source dataset
uspto-grants-1982_04
Patent number
US04325956

Reaction notes

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