Thioglycolic Acid → HCID 10248424, compound

HRID 1836345Notes

Reaction equation

HRID 1836345 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[SH:21][CH2:22][C:23](O)=[O:24]>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([N:18]2[C:23](=[O:24])[CH2:22][S:21][CH:9]2[C:8]2[CH:11]=[CH:12][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 78124-ChloroanilineHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 10248424HCID 10248424, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-methanesulfonylbenzaldehyde and 150 mg(1.18 mmol) of 4-chloroaniline were added and stirred in 10 ml of toluene and the mixture was heated and refluxed for 4 hours in the Dean-Stark trap apparatus. 0.083 ml(1.19 mmol) of mercaptoacetic acid was added to the reaction mixture and was heated and refluxed for 5 hours. The reaction mixture was cooled to room temperature and the solvent was distilled under reduced pressure and discarded, and then the resultant was diluted in 20 ml of ethyl acetate. The resultant was washed with 20 ml of 2N-hydrochloric acid, 20 ml of saturated sodium bicarbonate solution, and saturated sodium chloride solution and dried on anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate/n-hexane=1:1, v/v ) to give 230 mg of the title compound as an white crystal(yield 57.6%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 4 hours in the Dean-Stark trap apparatus
  3. temperaturewas heated
  4. temperaturerefluxed for 5 hours
  5. distillationthe solvent was distilled under reduced pressure
  6. additionthe resultant was diluted in 20 ml of ethyl acetate
  7. washThe resultant was washed with 20 ml of 2N-hydrochloric acid, 20 ml of saturated sodium bicarbonate solution, and saturated sodium chloride solution
  8. dry with materialdried on anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (ethyl acetate/n-hexane=1:1

Sources & evidence

ORD record
ord-5283344223df4b38859b3df7625f5ffe
Source dataset
uspto-grants-2004_08
Patent number
US06777434B2

Reaction notes

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