Hydrochloric Acid → HCID 54170692, compound

HRID 1417461Notes

Reaction equation

HRID 1417461 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[C:22]2[C:21]([S:23][CH3:24])=[C:20]([CH2:25][C:26]([O:28]CC3C=CC=CC=3)=[O:27])[CH:19]=[C:18]([CH3:36])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(O)C>[CH2:3]([N:10]1[C:22]2[C:21]([S:23][CH3:24])=[C:20]([CH2:25][C:26]([OH:28])=[O:27])[CH:19]=[C:18]([CH3:36])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54066300HCID 54066300, compound

Product 1

HCID 54170692HCID 54170692, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50 ml of ethanol and 50 ml of a 2N aqueous solution of sodium hydroxide was added to 1.16 g of benzyl (9-benzyl-4-methyl-1-methylthiocarbazol-2-yl)acetate, as obtained in Example 13a). The reaction mixture was stirred for 2 hours at room temperature, after which time it was acidified by adding a 1N aqueous solution of hydrochloric acid and then concentrated by evaporation under reduced pressure. Ethyl acetate was added to the residue thus obtained. The aqueous layer was extracted with ethyl acetate and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 20 g of silica gel with a 1:1 v/v mixture of hexane and ethyl acetate as the eluent, and then recrystallized from ethyl acetate and hexane, to yield 0.90 g of the title compound, melting at 219°-220° C.

Workup

  1. customas obtained in Example 13a)
  2. concentrationconcentrated by evaporation under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. customthus obtained
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. additionwith a 1:1 v/v mixture of hexane and ethyl acetate as the eluent
  11. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-87e72c52248e4b34a43ac7020dafc4b4
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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