Urea → 1-(2-Amino-1,3-oxazol-5-yl)ethan-1-one

HRID 1903065Notes

Reaction equation

HRID 1903065 reaction equation
Br[C:2]([C:5](=[O:7])[CH3:6])=[CH:3]O.[NH2:8][C:9]([NH2:11])=[O:10]>CC(C)=O>[C:5]([C:2]1[O:10][C:9]([NH2:11])=[N:8][CH:3]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 1176UreaHCID 573587893-Buten-2-one, 3-bromo-4-hydroxy-

Product 1

HCID 130828451-(2-Amino-1,3-oxazol-5-yl)ethan-1-oneYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 132.3 g (0.80 m) of 2-bromo-1-hydroxy-3-oxo-1-butene, 120.1 g (2.0 m) of urea, and 1.85 l of acetone was heated at reflux with overhead stirring for one hour. The mixture was concentrated and the oil residue was taken up into 600 ml of water, then made basic with concentrated ammonium hydroxide. After sitting at room temperature for 0.5 hour, a precipitate formed. This was collected, and dried in vacuo to give 61.1 g of crude product. The filtrate was again concentrated and the oil residue taken up in 50 ml of water and again made basic with concentrated ammonium hydroxide. After sitting overnight a second crop of crude product, amounting to 17.6 g was isolated. Both crops were combined and recrystallized from methanol to give 50.3 g (50%) of 5-acetyl-2-aminooxazole, m.p. 214°-215°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux with overhead
  3. concentrationThe mixture was concentrated
  4. waitAfter sitting at room temperature for 0.5 hour
  5. customa precipitate formed
  6. customThis was collected
  7. customdried in vacuo
  8. customto give 61.1 g of crude product
  9. concentrationThe filtrate was again concentrated
  10. waitAfter sitting overnight
  11. customa second crop of crude product, amounting to 17.6 g was isolated
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3b730f11ec24435b832af405451322b5
Source dataset
uspto-grants-1984_03
Patent number
US04435396

Reaction notes

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