Water → HCID 14050293, compound

HRID 1030229Notes

Reaction equation

HRID 1030229 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:16][C:17]([NH2:19])=[S:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Br[CH2:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].O>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:16][C:17]2[S:18][CH:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:19]=2)[CH:8]=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 66144Ethyl bromopyruvateHCID 13281940HCID 13281940, compound

Product 1

HCID 14050293HCID 14050293, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Di-tert-butyl-4-hydroxyphenylthiourea (2.60 g) and 2.01 g of ethyl bromopyruvate were dissolved in 100 ml of ethanol, and the solution was heated under reflux for 3 hours. After addition of water, the reaction mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution, then dried over magnesium sulfate, and concentrated. Purification of the crude product by silica gel column chromatography (chloroform-ethyl acetate=15:1) gave 1.80 g of the desired compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe reaction mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated aqueous sodium chloride solution, then dried over magnesium sulfate
  6. concentrationconcentrated
  7. customPurification of the crude product by silica gel column chromatography (chloroform-ethyl acetate=15:1)

Sources & evidence

ORD record
ord-af27894df15441c2944c1b8c9d67f17a
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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