Formaldehyde → HCID 19388451, compound

HRID 1460171Notes

Reaction equation

HRID 1460171 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 2.35 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 room temperature 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 1.63 g of crude crystals of the desired compound. The crude crystals were then dissolved in chloroform. To the chloroform solution was added ethanol in twice amount of the amount of the chloroform. Precipitated crystals 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 room temperature 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 1.63 g of crude crystals of the desired compound
  13. customPrecipitated crystals
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1532a5df675948969d2157c58d66efd3
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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