Formaldehyde → 3-(Hydroxymethyl)phenytoin

HRID 359864Notes

Reaction equation

HRID 359864 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:12][C:11]([OH:13])=[N:10][C:8]2=[O:9])=[CH:5][CH:6]=1.C=O.[C:22]([O-])([O-])=[O:23].[K+].[K+]>O>[C:14]1([C:7]2([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)[NH:12][C:11](=[O:13])[N:10]([CH2:22][OH:23])[C:8]2=[O:9])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 17755,5-DiphenylhydantoinHCID 11430Potassium Carbonate

Product 1

HCID 1613663-(Hydroxymethyl)phenytoinYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenytoin (5 g, 0.02 mol) was suspended in 180 mL of water; 20 mL of formaldehyde (37% solution) and 0.25 g K2CO3 were added and the mixture was stirred at 25°-30° C. for 24 hours. The white solid which formed was removed by filtration and washed repeatedly with a 3% solution of formaldehyde, then air-dried for 3 to 4 hours and over P2O5 in a vacuum dessicator. Yield 91-93%, m.p. 185°-189° C. Anal. calc. for C16H14N2O3 : C, 68.07; H, 5.00; N, 9.93. Found: C, 67.97; H, 5.05; N, 9.93. The product had the formula: ##STR71##

Workup

  1. customThe white solid which formed
  2. customwas removed by filtration
  3. washwashed repeatedly with a 3% solution of formaldehyde
  4. dry with materialair-dried for 3 to 4 hours and over P2O5 in a vacuum dessicator

Sources & evidence

ORD record
ord-196b9ca803504e88b67123cf4634d6aa
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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