Hydantoin → 5-[(3-Phenylmethoxy-4-methoxyphenyl)methylene]-2,4-imidazolidinedione

HRID 1660516Notes

Reaction equation

HRID 1660516 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:25][C:23](=[O:24])[NH:22][C:20]1=[O:21].C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:25]3[NH:19][C:20](=[O:21])[NH:22][C:23]3=[O:24])[CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10006HydantoinHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 538290325-[(3-Phenylmethoxy-4-methoxyphenyl)methylene]-2,4-imidazolidinedioneYield 45.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 24.43 g (100 moles) of 3-phenylmethoxy-4-methoxybenzaldehyde (Berichte 67, 1214/1934/), 10.01 g. (100 mmoles) of hydantoin, 38 ml of anhydrous acetic acid and 19.5 g of anhydrous sodium acetate is heated to 140° C. with shaking and the solution obtained is refluxed at 158°-162° C. for 2.5 hours, then cooled and poured into 250 ml of ice-water. The gum obtained becomes crystalline after 30 minutes. The crystals are filtered, washed successively with water, ethanol and ether and dried to give 14.75 g (45.5%) of the title compound, m.p. 249°-251° C.

Workup

  1. customthe solution obtained
  2. temperatureis refluxed at 158°-162° C. for 2.5 hours
  3. temperaturecooled
  4. customThe gum obtained
  5. filtrationThe crystals are filtered
  6. washwashed successively with water, ethanol and ether
  7. customdried

Sources & evidence

ORD record
ord-73f09316f329441bbe70c2b8ab689d4c
Source dataset
uspto-grants-1981_12
Patent number
US04308278

Reaction notes

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