Acetic Anhydride → 6-Amino-1-propyluracil

HRID 1381852

Reaction equation

HRID 1381852 reaction equation
[C:1](CC(O)=O)#[N:2].[CH2:7]([NH:10][C:11]([NH2:13])=[O:12])[CH2:8][CH3:9].C(O[C:18](=[O:20])[CH3:19])(=O)C>>[NH2:2][C:1]1[N:10]([CH2:7][CH2:8][CH3:9])[C:11](=[O:12])[NH:13][C:18](=[O:20])[CH:19]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 12303Propylurea

Product 1

HCID 1045626-Amino-1-propyluracil

Procedure

To a solution of 47 g (0.55 mol) cyanoacetic acid and 100 ml of acetic anhydride was added 50 g (0.49 mol) of n-propylurea. The solution was stirred at 60°-70° C. for 1 hour. After cooling; white crystals were filtered off and washed with ethanol. Yield 56.2 g (68%) (I). This was stirred in 100 ml of hot water and 60 ml of 2N 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 5N HCl. After cooling, white crystals were filtered off. Yield 34.3 g (61%) (II) NMR.

Workup

  1. temperatureAfter cooling
  2. filtrationwhite crystals were filtered off
  3. washwashed with ethanol
  4. stirringThis was stirred in 100 ml of hot water
  5. addition60 ml of 2N 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-c68cad846c234caebdb70c588c68a857
Source dataset
uspto-grants-1989_02
Patent number
US04804664

Linked notes

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