Formaldehyde → 3-(Hydroxymethyl)phenytoin

HRID 972081Notes

Reaction equation

HRID 972081 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[C:22](=O)([O-])[O-:23].[K+].[K+]>O>[OH:23][CH2:22][N:9]1[C:8](=[O:13])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:11][C:10]1=[O:12]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 17755,5-DiphenylhydantoinHCID 11430Potassium Carbonate

Product 1

HCID 1613663-(Hydroxymethyl)phenytoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 g of 5,5-diphenylhydantoin (0.08 moles) and 80 ml (32 g) of formalin are introduced into a suitable reaction vessel containing 720 ml of water and one g of potassium carbonate. The reaction is stirred at room temperature for 24 hours, after which the subject compound, mp 186.5°-188.5° C., yield 22.58 g (91.86%) is obtained by filtration.

Workup

  1. customafter which the subject compound, mp 186.5°-188.5° C., yield 22.58 g (91.86%) is obtained by filtration

Sources & evidence

ORD record
ord-cf2d76f527284f3cbacb2000501b9e3a
Source dataset
uspto-grants-1979_07
Patent number
US04163058

Reaction notes

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