Sodium Carbonate → HCID 19388440, compound

HRID 1757564Notes

Reaction equation

HRID 1757564 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[N:10]1([C:16]([S:18][CH3:19])=[S:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][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][CH3:19])=[S:17])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11093alpha-Chloro-o-xyleneHCID 21278808Methyl piperazine-1-carbodithioate

Product 1

HCID 19388440HCID 19388440, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.405 g (10 mmol.) of 2-methylbenzyl chloride, 1.76 g (10 mmol.) of methyl 1-piperazinecarbodithioate, 1.06 g (10 mmol.) of anhydrous sodium carbonate and 14 ml of ethanol. The mixtrue was refluxed under heating for2.5 hours. Ethanol was distilled off under reduced pressure. The residue was mixed with water and ether. The organic solvent portion was taken out,and to the portion was added 15 ml of 8-N hydrochloric acid. The aqueous portion was neutralized with 1-N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate portion was washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill offthe solvent. The residue was purified over a silica gel column to give 790 mg of methyl 4-(2-methylbenzyl)-1-piperazinecarbodithioate as a white crystalline product, yield 28.2%.

Workup

  1. temperatureThe mixtrue was refluxed
  2. temperatureunder heating for2
  3. custom5 hours
  4. distillationEthanol was distilled off under reduced pressure
  5. additionThe residue was mixed with water and ether
  6. additionwas added 15 ml of 8-N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate portion was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  10. distillationto distill offthe solvent
  11. customThe residue was purified over a silica gel column

Sources & evidence

ORD record
ord-9132d7c95df843e8bbb371fdd6b69df8
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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