Formaldehyde → HCID 15290077, compound

HRID 1757526Notes

Reaction equation

HRID 1757526 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N:12]1([C:18]([S:20][CH3:21])=[S:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[CH2:22]=O>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:6]=1)[CH2:22][N:15]1[CH2:16][CH2:17][N:12]([C:18]([S:20][CH3:21])=[S:19])[CH2:13][CH2:14]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 960094-HydroxyphenylacetateHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 15290077HCID 15290077, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 5 ml of chloroform were added 152 mg of 4-acetoxyphenol, 211 mg of methyl 1-piperazinecarbodithioate and 36 mg of paraformaldehyde. The resulting mixture was refluxed for 4 hours. The mixture was cooled, and tothis was added chloroform. The mixture was then washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and placed under reduced pressure to distill of the solvent. The residue was purified by siica gel column chromatography to yield an oil. The oil was crystallized by addition of ethanol. The obtained crystals were collected by filtration to give 224 mg of the desired compound as a white crystalline product, m.p. 124° C., yield 65.9%.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. washThe mixture was then washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. distillationto distill of the solvent
  6. customThe residue was purified by siica gel column chromatography
  7. customto yield an oil
  8. customThe oil was crystallized by addition of ethanol
  9. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-b279cdf584064b408b9ba6ec67e532c0
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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