Formaldehyde → HCID 23338218, compound

HRID 971909Notes

Reaction equation

HRID 971909 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.[CH2:20]=[O:21].N(CCO)(CCO)C[CH2:24][OH:25]>O1CCOCC1.O>[OH:25][CH2:24][N:11]1[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)[C:8](=[O:13])[N:9]([CH2:20][OH:21])[C:10]1=[O:12]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 17755,5-DiphenylhydantoinHCID 7618Triethanolamine

Product 1

HCID 23338218HCID 23338218, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

In accordance with Example 5 of U.S. Pat. No. 3,595,862, 50.4 g (0.2 mole) of 5,5-diphenylhydantoin were suspended in a mixture of 50 ml of dioxan and 200 ml of water. To this suspension were added 88 ml of 37% aqueous formaldehyde solution and 10 ml of triethanolamine and the mixture was stirred for 7 hours at 92°-98° C. The resultant clear, colourless solution was cooled to 25° C., adjusted to a pH of 1 and extracted with ether (3 × 100 ml). The ethereal solution was washed with 50 ml of saturated saline solution and dried over anhydrous sodium sulphate. The ether was distilled off under reduced pressure (bath temperature 40° C.) and the 1,3-di-(hydroxymethyl)-5,5-diphenylhydantoin is obtained as an oil in a yield of 63.1 g (99.8% of theory).

Workup

  1. extractionextracted with ether (3 × 100 ml)
  2. washThe ethereal solution was washed with 50 ml of saturated saline solution
  3. dry with materialdried over anhydrous sodium sulphate
  4. distillationThe ether was distilled off under reduced pressure (bath temperature 40° C.)

Sources & evidence

ORD record
ord-3ec75aa66d744e26a32b1ed1695a869a
Source dataset
uspto-grants-1979_07
Patent number
US04161594

Reaction notes

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