Formaldehyde → HCID 20369675, compound

HRID 616319Notes

Reaction equation

HRID 616319 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[O:9]2)=[CH:4][CH:3]=1.[CH2:15]=[O:16].O>CO.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:15][OH:16])[C:10](=[O:14])[O:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 12809633HCID 12809633, compound

Product 1

HCID 20369675HCID 20369675, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-(4-Methylphenyl)-1,2,4-oxadiazolidin-3,5-dione (0.05 mole) dissolved in methanol (100 ml) and aqueous formaldehyde (37% conc.; 0.06 mole) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux, with stirring for a period of about 2 hours. After this time the reaction mixture is stripped of methanol and water, leaving a residue. This residue is dissolved in methylene chloride, and the resulting solution is washed with water. The washed solution is dried over anhydrous magnesium sulfate, filtered and stripped of solvent to yield the desired product 2-(4-methylphenyl)-4-hydroxymethyl-1,2,4-oxadiazolidin- 3,5-dione.

Workup

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

Sources & evidence

ORD record
ord-a47a39e534804b88ba5dff2509ab7d5d
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

Loading…