Formaldehyde → HCID 54065540, compound

HRID 616323Notes

Reaction equation

HRID 616323 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:16]=[O:17].O>CO.C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:16][OH:17])[C:11](=[O:15])[O:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 53802233HCID 53802233, compound

Product 1

HCID 54065540HCID 54065540, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-(3-methylthiophenyl)-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-(3-methylthiophenyl)-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-d609d4ef505942169bb4fee8a44e67a7
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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