Sodium Carbonate → HCID 54287733, compound

HRID 1460194Notes

Reaction equation

HRID 1460194 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[N:10]1([C:16]([S:18]C)=S)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[C:20](=O)([O-])[O-:21].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:13]1[CH2:14][CH2:15][N:10]([C:16](=[S:18])[O:21][CH3:20])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 119062-Chlorobenzyl chlorideHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 54287733HCID 54287733, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 16 ml of ethanol, 1.61 g (10 mmol.) of 2-chlorobenzyl chloride, 1.76 g (10 mmol.) of methyl 1-piperazinecarbodithioate and 1.06 g (10 mmol.) of sodium carbonate were heated to reflux for 4 hours. Ethanol was distilled off under reduced pressure, and to the residue was added water. The aqueous mixture was extracted with 30 ml of ether. The ether extract was shaken with 15 ml of 3N-hydrochloric acid. There were separated three layers. The aqueous portion and the oil portion were taken out and combined. The combined mixture was made alkaline with 1-N aqueous sodium hydroxide solution and extracted with ether. The ether portion was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill off the solvent. The residue was purified over a silica gel column to give 1.03 g of methyl 4-(2-chlorobenzyl)-1-piperazinecarbothioate as a pale brown oil, yield 34.3%.

Workup

  1. temperatureto reflux for 4 hours
  2. distillationEthanol was distilled off under reduced pressure
  3. additionto the residue was added water
  4. extractionThe aqueous mixture was extracted with 30 ml of ether
  5. extractionThe ether extract
  6. customThere were separated three layers
  7. extractionextracted with ether
  8. washThe ether portion was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationto distill off the solvent
  11. customThe residue was purified over a silica gel column

Sources & evidence

ORD record
ord-57b991351107440e9f98bb0fe411d544
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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