Formaldehyde → HCID 19388487, compound

HRID 1757536Notes

Reaction equation

HRID 1757536 reaction equation
[CH2:1]=O.[N:3]1([C:9]([S:11][CH3:12])=[S:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH3:13][O:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=1[OH:23]>C(O)C>[CH3:13][O:14][C:15]1[C:16]([OH:23])=[C:17]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:1][N:6]1[CH2:7][CH2:8][N:3]([C:9]([S:11][CH3:12])=[S:10])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 788282,3-DimethoxyphenolHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388487HCID 19388487, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

In 10 ml of ethanol was dissolved 0.86 g of 35% formalin. To the solution was dropwise added under chilling with ice a solution of 2.35 g of methyl 1-piperazinecarbodithioate in 5 ml of ethanol. The mixture was then stirred for 30 min. at room temperature. The mixture was refluxed overnight under heating after addition of a solution of 1.54 g of 2,3-dimethoxyphenol in 5 ml of ethanol under chilling with ice. The reaction mixture was cooled to room temperature. The solvent was distilledoff under reduced pressure, and the residue was purified by silica gel column chromatography. The eluate was treated with 10 ml of ethanol to obtain a crystalline product. The product was collected by filtration and washed with ethanol to give 1.76 g of the desired compound as a pale yellow crystalline product, m.p. 113° C. (decomp.), yield 51.5%.

Workup

  1. additionTo the solution was dropwise added
  2. temperatureThe mixture was refluxed overnight
  3. temperatureunder heating
  4. temperatureunder chilling with ice
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customthe residue was purified by silica gel column chromatography
  7. additionThe eluate was treated with 10 ml of ethanol
  8. customto obtain a crystalline product
  9. filtrationThe product was collected by filtration
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-2b7925f2a9e1438682681a4b84918dcb
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

Loading…