Formaldehyde → HCID 19388451, compound

HRID 1757537Notes

Reaction equation

HRID 1757537 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.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.C(Cl)(Cl)Cl>[OH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[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

6

Reactant 3

HCID 712FormaldehydeHCID 996PhenolHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388451HCID 19388451, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent4×HCID 6212ChloroformSolvent3×

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 2.85 g of methyl 1-piperazinecarbodithioate in 4 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 2.82 g of phenol in 4 ml of ethanol under chilling with ice and subsequent stirring at roomtemperature for 3 hours, The reaction mixture was cooled to room temperature. A half amount of the solvent was distilled off under reduced pressure. To the residue was added 5 ml of ether to precipitate crystals. The crystals were collected by filtration and washed with 15 ml of ether to give 1.68 g of crude crystals of the desired compound. The crude crystals were then dissolved in chloroform. To the chloroform solution wasadded ethanol in twice amount of the amount of the chloroform. Precipitatedcrystals were collected by filtration to give 0.95 g of the desired compound as a white crystalline product, m.p. 147° C., yield 33.4%.

Workup

  1. additionTo the solution was dropwise added
  2. temperatureThe mixture was refluxed overnight
  3. temperatureunder heating
  4. temperatureunder chilling with ice
  5. stirringsubsequent stirring at roomtemperature for 3 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. distillationA half amount of the solvent was distilled off under reduced pressure
  8. additionTo the residue was added 5 ml of ether
  9. customto precipitate crystals
  10. filtrationThe crystals were collected by filtration
  11. washwashed with 15 ml of ether
  12. customto give 1.68 g of crude crystals of the desired compound
  13. filtrationPrecipitatedcrystals were collected by filtration

Sources & evidence

ORD record
ord-2f907a3b335146ab84a36324fd352f9d
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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