Formaldehyde → HCID 20369667, compound

HRID 616329Notes

Reaction equation

HRID 616329 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[S:14])[NH:12][C:11](=[S:15])[O:10]2)=[CH:5][CH:4]=1)#[N:2].[CH2:16]=[O:17].O>CO.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13](=[S:14])[N:12]([CH2:16][OH:17])[C:11](=[S:15])[O:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 20369672HCID 20369672, compound

Product 1

HCID 20369667HCID 20369667, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2-(4-Cyanophenyl)-1,2,4-oxadiazolidin-3,5-dithione (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-cyanophenyl)-4-hydroxymethyl-1,2,4-oxadiazolidin-3,5-dithione.

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-334d980355e54a97aa895e979fcb0fbe
Source dataset
uspto-grants-1978_02
Patent number
US04073894

Reaction notes

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