Ethyl bromopyruvate → HCID 18408534, compound

HRID 992984Notes

Reaction equation

HRID 992984 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](=[S:8])[NH2:7].Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH3:15][O:14][C:10]1[CH:9]=[C:5]([C:6]2[S:8][CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:7]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 3033195Benzamide, thio-3,4,5-trimethoxy-

Product 1

HCID 18408534HCID 18408534, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3,4,5-Trimethoxybenzothioamide (2.5 g) and 90% ethyl bromopyruvate (2.62 g) were added to ethanol (20 mL), and the mixture was stirred at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) and further recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)
  7. customfurther recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-90fdfa3d5b914add8cb01dc678b44b18
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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