Benzyl chloromethyl ether → 3-Benzyloxymethyl-5,5-diphenylhydantoin

HRID 1759181Notes

Reaction equation

HRID 1759181 reaction equation
[Na].[C:2]1([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O>[CH2:24]([O:23][CH2:22][N:10]1[C:9](=[O:14])[C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:12][C:11]1=[O:13])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 137983Benzyl chloromethyl etherHCID 97955475,5-Diphenylhydantoin sodium

Product 1

HCID 130352753-Benzyloxymethyl-5,5-diphenylhydantoin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,5-Diphenylhydantoin sodium (27.5 g) was suspended in 250 ml of dimethylformamide. To the suspension was added 15 ml of chloromethylbenzylether with good stirring and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into 1 liter of ice cold water and stirred for one hour. The solid product was removed by filtration and dissolved in 150 ml of hot ethanol. To the boiling solution 1 g of activated carbon was added and the hot solution was filtered through a Buchner funnel which contained a compacted layer of finely-divided diatomaceous silica. The cake was washed three times with 10 ml of ethanol and the hot solution together with the washings was allowed to cool to room temperature. The resulting crystals were filtered and recrystallized two more times in the same manner as described for the first crystallization. There was obtained 13.1 g of 3-benzyloxymethyl-5,5-diphenylhydantoin, m.p. 151°-152°.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringstirred for one hour
  3. customThe solid product was removed by filtration
  4. dissolutiondissolved in 150 ml of hot ethanol
  5. additionTo the boiling solution 1 g of activated carbon was added
  6. filtrationthe hot solution was filtered through a Buchner funnel which
  7. washThe cake was washed three times with 10 ml of ethanol
  8. filtrationThe resulting crystals were filtered
  9. customrecrystallized two more times in the same manner
  10. customas described for the first crystallization

Sources & evidence

ORD record
ord-795eb468d1684c01961f6944ebea22e5
Source dataset
uspto-grants-1982_07
Patent number
US04339454

Reaction notes

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