p-Toluenesulfonic acid → HCID 69181424, compound

HRID 351280Notes

Reaction equation

HRID 351280 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=O>C1C=CC=CC=1>[CH2:27]([O:26][C:20](=[O:25])[CH:21]=[C:22]([NH:17][C:16]1[CH:18]=[CH:19][C:13]([CH3:12])=[CH:14][CH:15]=1)[CH3:24])[CH3:28]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7813p-ToluidineHCID 8868Ethyl Acetoacetate

Product 1

HCID 69181424HCID 69181424, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Toluenesulfonic acid (catalytic amount) was added to a solution of p-methylaniline (10.7 g, 100 mmol) and ethyl acetoacetate (13.0 g, 110 mmol) in benzene (250 mL) at room temperature. The reaction mixture was refluxed with a Dean-Stark apparatus over night. After cooling down to room temperature, the reaction mixture was concentrated and purified by column chromatography (5% ethyl acetate in n-hexane) to give 3-p-tolylamino-but-2-enoic acid ethyl ester (18.6 g, 85% yield).

Workup

  1. temperatureThe reaction mixture was refluxed with a Dean-Stark apparatus over night
  2. concentrationthe reaction mixture was concentrated
  3. custompurified by column chromatography (5% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-fcbf5cade4ac42189317a4b0e526439c
Source dataset
uspto-grants-2007_02
Patent number
US07183413B2

Reaction notes

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