Formaldehyde → Methyl 4-(2-hydroxy-5-methoxybenzyl)-1-piperazinecarbodithioate

HRID 1757532Notes

Reaction equation

HRID 1757532 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[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>C(O)C>[OH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][C:17]=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

5

Reactant 3

HCID 712FormaldehydeHCID 90154-MethoxyphenolHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388436Methyl 4-(2-hydroxy-5-methoxybenzyl)-1-piperazinecarbodithioateYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 20 ml of ethanol was 1.05 g of 37% formalin, and to the mixture was added under chilling with ice 2.29 g of methyl 1-piperazinecarbodithioate.The mixture was then stirred for 30 min. at room temperature, and, after addition of 1.24 g of 4-methoxyphenol, refluxed overnight under heating. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained oil was crystallized from 10 ml of ethanol. The crystals were collected by filtration and subsequently washed with ethanol to give 1.06 g of the desired compound as white crystals, m.p. 112° C., yield 34%.

Workup

  1. additionto the mixture was added
  2. temperaturerefluxed overnight
  3. temperatureunder heating
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. customThe obtained oil was crystallized from 10 ml of ethanol
  7. filtrationThe crystals were collected by filtration
  8. washsubsequently washed with ethanol

Sources & evidence

ORD record
ord-ff4d30981a7a4a5692f88990382ebfac
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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