Acetic Anhydride → 6-Amino-1-propyluracil

HRID 2285898Notes

Reaction equation

HRID 2285898 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 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 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 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-ed8ab31212104ac9971a7f4c355e51d0
Source dataset
uspto-grants-1982_04
Patent number
US04325956

Reaction notes

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