Formaldehyde → HCID 20369664, compound

HRID 616316Notes

Reaction equation

HRID 616316 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[NH:10][C:9](=[O:13])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]=[O:15].O>CO.C(Cl)Cl>[C:1]1([N:7]2[C:11](=[O:12])[N:10]([CH2:14][OH:15])[C:9](=[O:13])[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 15620455N-PHENYL-3,5-OXADIAZOLIDIONE

Product 1

HCID 20369664HCID 20369664, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-Phenyl-1,2,4-oxadiazolidin-3,5-dione (6.75 grams; 0.044 mole) dissolved in methanol (100 ml) and aqueous formaldehyde (5.67 ml of 37% conc.; 0.06 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux, with stirring for a period of about 2 hours. After this time the reaction mixture was stripped of methanol and water to yield a solid residue. The residue was then dissolved in methylene chloride, and the resulting solution was washed with water. The washed solution was dried over anhydrous magnesium sulfate and stripped of solvent to yield the desired product 2-phenyl-4-hydroxymethyl-1,2,4-oxadiazolidin-3,5-dione as a solid residue.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux
  5. customto yield a solid residue
  6. washthe resulting solution was washed with water
  7. dry with materialThe washed solution was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-aac74f6b5a014ee1bd9087154ca51db9
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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