Methanol → HCID 19388484, compound

HRID 1757525Notes

Reaction equation

HRID 1757525 reaction equation
[CH3:1]O.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]([S-:17])=[S:16])[CH2:11][CH2:10]1.[Na+].CI>O>[CH3:24][O:23][C:19]1[CH:18]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[C:20]=1[O:21][CH3:22])[CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]([S:17][CH3:1])=[S:16])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 6328Methyl iodideHCID 23665402HCID 23665402, compound

Product 1

HCID 19388484HCID 19388484, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 70 ml of methanol containing 6.67 g of sodium 4-(3,4,5-trimethoxybenzyl)piperazinecarbodithioate was dropwise added under chilling with ice 20 ml of methanol solution containing 2.6 g of methyl iodide for 20 min. The resulting mixture was further stirred for 3 hours under chilling with ice. The reaction solution was placed under reduced pressure to distill off the solvent, leaving a residue. The residue was dissolved in water, and then extracted with chloroform. The chloroform 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. Thus obtained crude product was purified by silica gel chromatography to give 3.7 g of the desired compound as a pale yellow crystalline product.

Workup

  1. temperatureunder chilling with ice
  2. distillationto distill off the solvent
  3. customleaving a residue
  4. extractionextracted with chloroform
  5. washThe chloroform portion was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationto distill off the solvent
  8. customThus obtained crude product
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-09e54ae47dce4b93bf486448abe69efb
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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