Urea → 5-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trione

HRID 993079Notes

Reaction equation

HRID 993079 reaction equation
[O-:1][CH2:2]C.[Na+].[O:5]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21]CC)=O)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:24][C:25]([NH2:27])=[O:26]>C(O)C>[O:5]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[C:19](=[O:21])[NH:27][C:25](=[O:26])[NH:24][C:2]2=[O:1])=[CH:16][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 13567666Ethyl 2-(4-phenoxyphenyl)acetate

Product 1

HCID 116737785-(4-Phenoxyphenyl)-1,3-diazinane-2,4,6-trioneYield 21.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A soultion of sodium ethoxide (0.27 g) in 3 ml of anhydrous ethanol is added with 0.657 g of ethyl (4′-phenoxyphenyl)acetate dissolved in 5 ml of ethanol, then with urea (0.18 g). The reaction mixture is refluxed for 2 hours 30 minutes, then it is cooled to room temperature and the suspended solid is filtered. The solid is redissolved in 8 ml of water and the solution is acidified with 1 N hydrochloric acid. The solid which separates is recovered by filtration to give 0.165 g of the product, m.p. >240° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours 30 minutes
  2. filtrationthe suspended solid is filtered
  3. dissolutionThe solid is redissolved in 8 ml of water
  4. filtrationThe solid which separates is recovered by filtration

Sources & evidence

ORD record
ord-03457166ea43486e9d881a03e7e5160d
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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