Hydrochloric Acid → HCID 19388522, compound

HRID 1757544Notes

Reaction equation

HRID 1757544 reaction equation
Cl.CO.[OH:4][C:5]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:6]=1[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([S:16][CH3:17])=[S:15])[CH2:10][CH2:9]1>O>[C:5]1(=[O:4])[CH:21]=[CH:20][C:19](=[O:22])[CH:18]=[C:6]1[CH2:7][N:8]1[CH2:9][CH2:10][N:11]([C:14]([S:16][CH3:17])=[S:15])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 19388478HCID 19388478, compound

Product 1

HCID 19388522HCID 19388522, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a mixture of 6.8 ml of 1-N hydrochloric acid and 6.8 ml of methanol was dissolved 680 mg of methyl 4-(2,5-dihydroxybenzyl)-1-piperazinecarbodithioate. The resulting solutionwas chilled with ice, and to this was drowpise added a solution of 1.24 g (5.3 mmol.) of FeCl3.6H2O in 4.3 ml of water for 15 min. To this was further added 25 ml of methanol. To thus obtained homogeneous solution was again added a solution of 2.2 g of FeCl3.6H2O in 10 ml of water. The mixture was then stirred for 10 min. and placed under reduced pressure to distill off methanol. To the residue was added 50 ml of chloroform, and to this was added a saturated sodium hydrogen carbonateto adjust pH of the mixture to 7. Insolubles were removed by filtration. The organic solvent portion was taken out, 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. Theresidue was then purified by silica gel column chromatography to give 234 mg of the desired compound as a yellow powder, m.p. 115°-116° C. (decomp.), yield 38.9%.

Workup

  1. temperatureThe resulting solutionwas chilled with ice
  2. distillationto distill off methanol
  3. additionTo the residue was added 50 ml of chloroform
  4. additionto this was added a saturated sodium hydrogen
  5. customInsolubles were removed by filtration
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  8. distillationto distill off the solvent
  9. customTheresidue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c44b64763334418a8b0187fdf994164d
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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