Sodium Carbonate → HCID 19388448, compound

HRID 1460188Notes

Reaction equation

HRID 1460188 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5]Cl.[N:13]1([C:19]([S:21][CH3:22])=[S:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][N:16]1[CH2:17][CH2:18][N:13]([C:19]([S:21][CH3:22])=[S:20])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2911942,5-Dimethoxybenzyl chlorideHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388448HCID 19388448, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 2.20 g (11.8 mmol.) of 2,5-dimethoxybenzyl chloride, 2.19 g (11.8 mmol.) of methyl 1-piperazinecarbodithioate, 1.25 g (11.8 mmol.) of anhydrous sodium carbonate and 15 ml of ethanol were mixed and refluxed under heating for 18 hours. Insolubles were removed by filtration. The solvent of the filtrate was distilled off under reduced pressure. To the residue were added 15 ml of dichloromethane and 15 ml of water. The organic solvent portion was taken out, washed with 15 ml of 1-N hydrochloric acid and 18 ml of 1-N aqueous sodium hydroxide solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by column chromatography to give 1.23 g of methyl 4-(2,5-dimethoxybenzyl)-1-piperazinecarbodithioate, yield 31.9%.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 18 hours
  3. customInsolubles were removed by filtration
  4. distillationThe solvent of the filtrate was distilled off under reduced pressure
  5. additionTo the residue were added 15 ml of dichloromethane and 15 ml of water
  6. washwashed with 15 ml of 1-N hydrochloric acid and 18 ml of 1-N aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was then distilled off under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a4f56e9c7377469cba392b894b73ad35
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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