Hydrochloric Acid → HCID 19388522, compound

HRID 1460178Notes

Reaction equation

HRID 1460178 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 solution was chilled with ice, and to this was dropwise 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 carbonate to 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. The residue 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 solution was 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 carbonate
  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. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04362a6f766644369ac00fad144fc82b
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

Loading…