Acetic Anhydride → HCID 833803, compound

HRID 1421236Notes

Reaction equation

HRID 1421236 reaction equation
[CH2:1]([NH:7][C:8]([NH2:10])=[O:9])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14](O)=[O:15])#[N:12].C(OC(=O)C)(=O)C>O>[NH2:12][C:11]1[N:7]([CH2:1][C:2]2[O:6][CH:5]=[CH:4][CH:3]=2)[C:8](=[O:9])[NH:10][C:14](=[O:15])[CH:13]=1

Participants

5

Procedure

A solution of furfurylurea (7.0 g, 50.0 mmol), cyanoacetic acid (4.7 g, 55.0 mmol), and acetic anhydride (50 ml) was heated to 95° C. for 3 hours. After cooling to ambient temperature the solution was concentrated under reduced pressure to give a crude intermediate that was stirred with water (30 ml). After concentrating, the residue was dissolved in water (100 ml) and treated with a 50% aqueous sodium hydroxide solution (10 ml) to give a pH of 13. This solution was heated at 70° C. for 30 minutes, cooled and filtered. The wet solids were stirred in boiling ethanol for 15 minutes, cooled to ambient temperature and filtered. The filtrate was evaporated under reduced pressure to give 6-amino-1-furfuryluracil (5.5 g, 53% yield) as an orange solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto give a crude intermediate
  3. concentrationAfter concentrating
  4. dissolutionthe residue was dissolved in water (100 ml)
  5. additiontreated with a 50% aqueous sodium hydroxide solution (10 ml)
  6. customto give a pH of 13
  7. temperatureThis solution was heated at 70° C. for 30 minutes
  8. temperaturecooled
  9. filtrationfiltered
  10. customfor 15 minutes
  11. temperaturecooled to ambient temperature
  12. filtrationfiltered
  13. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8283b5e8dd554cfe92b7ef602c0459eb
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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