Hydrochloric Acid → HCID 19388502, compound

HRID 1757551Notes

Reaction equation

HRID 1757551 reaction equation
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[C:16]([OH:23])=[C:15]([CH3:24])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([S:13][CH3:14])=[S:12])[CH2:7][CH2:6]1.Cl.CO>O>[CH3:22][O:21][C:17]1[C:16](=[O:23])[C:15]([CH3:24])=[C:3]([CH2:4][N:5]2[CH2:6][CH2:7][N:8]([C:11]([S:13][CH3:14])=[S:12])[CH2:9][CH2:10]2)[C:2](=[O:1])[C:18]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19388426HCID 19388426, compound

Product 1

HCID 19388502HCID 19388502, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 700 mg (1.88 mmol.) of methyl 4-(2,5-dihydroxy-3,4-dimethoxy-6-methylbenzyl)-1-piperazinecarbodithioate were added 7 ml of 1-N hydrochloric acid and 17 ml of methanol. The mixture was chilled with ice, and to the mixture was dropwise added a solution of 1.76 g (7.52 mmol.) of FeCl3.6H2O in 5 ml of water.The resulting homogeneous red-colored solution was stirred for 30 min. and placed under reduced pressure at a temperature of lower than 50° C.to distill off methanol. To the residue was added 50 ml of ethyl acetate, and further added portionwise a saturated aqueous sodium hydrogen carbonate solution to adjust the solution to pH 10. A precipitated brownish red solid was removed by filtration. Thus obtained organic filtrate 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 crystallized from ethanol, and collected by filtration, to give 540 mg of the desired compound as an orange-brown crystalline powder, m.p. 115°-116° C., yield 77.6%.

Workup

  1. temperatureThe mixture was chilled with ice
  2. customlower than 50° C
  3. distillationto distill off methanol
  4. additionTo the residue was added 50 ml of ethyl acetate
  5. additionfurther added portionwise a saturated aqueous sodium hydrogen carbonate solution
  6. customA precipitated brownish red solid was removed by filtration
  7. washThus obtained organic filtrate 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 crystallized from ethanol
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ccc47bfb030846e594b2b8ad27254693
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

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