Sodium Carbonate → HCID 19388440, compound

HRID 1460197Notes

Reaction equation

HRID 1460197 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 mixture was refluxed under heating for 2.5 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 3-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 off the 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 mixture was refluxed
  2. temperatureunder heating for 2.5 hours
  3. distillationEthanol was distilled off under reduced pressure
  4. additionThe residue was mixed with water and ether
  5. additionto the portion was added 15 ml of 3-N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate portion was washed with water
  8. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  9. distillationto distill off the solvent
  10. customThe residue was purified over a silica gel column

Sources & evidence

ORD record
ord-c9fd1bcd20db47ab90869469cef3c022
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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