Acetic Acid → HCID 22481953, compound

HRID 2181616Notes

Reaction equation

HRID 2181616 reaction equation
[CH2:1]([O:8][CH:9]([CH3:19])[C:10]([NH:12][C:13]([NH:15][C:16]([NH2:18])=[O:17])=[O:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)(=O)C>O>[CH2:1]([O:8][CH:9]([C:10]1[NH:12][C:13](=[O:14])[NH:15][C:16](=[O:17])[N:18]=1)[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 22481944HCID 22481944, compound

Product 1

HCID 22481953HCID 22481953, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an ice-cold suspension of 2-benzyloxy-N-ureidocarbonyl-propionamide (9.4 mmol, 2.5 g) in water (15 mL) was added KOH (28 mmol, 1.6 g) in water (10 mL). The reaction temperature was slowly raised to room temperature, and the reaction was allowed to stir for 1 h. Sufficient acetic acid was added to adjust the pH of the reaction to 5, and the resulting cloudy solution was extracted with chloroform (3×20 mL). The chloroform layer was collected, dried, filtered and the filtrate was concentrated to obtain a residue, which was triturated with isopropyl ether to obtain 6-(1-benzyloxy-ethyl)-1H-[1,3,5]triazine-2,4-dione (74%, 1.72 g); NMR 1.4 (d, 3H), 4.2 (t, 1H), 4.6 (dd, 2H), 7.4 (m, 5H), 11.2 (s, 1H), 12.1 (s, 1H).

Workup

  1. customthe pH of the reaction to 5
  2. extractionthe resulting cloudy solution was extracted with chloroform (3×20 mL)
  3. customThe chloroform layer was collected
  4. customdried
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto obtain a residue, which
  8. customwas triturated with isopropyl ether

Sources & evidence

ORD record
ord-de8699f29fab4c19b0edf2f09df5b390
Source dataset
uspto-grants-2005_05
Patent number
US06894047B2

Reaction notes

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