p-Toluenesulfonic acid → HCID 70109536, compound

HRID 1708573Notes

Reaction equation

HRID 1708573 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[F:13][C:14]([F:24])([F:23])[C:15](=O)[CH2:16][C:17]([O:19][CH2:20]C)=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:12][O:11][C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:15]([C:14]([F:24])([F:23])[F:13])=[CH:16][C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2761030Methyl 2-(4-aminophenyl)acetate

Product 1

HCID 70109536HCID 70109536, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl p-aminophenylacetate (7 g), ethyl trifluoroacetoacetate (8.19 g) and p-toluenesulfonic acid (500 mg) were dissolved into benzene (100 ml) and, providing Dean Stalk dehydrating apparatus placed molecular sieve (MS 4 angstroms) therein, the solution was refluxed for 10 hours under heat. Solvent was distilled off under reduced pressure and the residue was purified by means of silica gel column chromatography (development solvent: ethyl acetate:hexane=1:4) to obtain methyl 3-(4-methoxycarbonylmethylphenylamino)-3-trifluoromethylacrylate (7.18 g) as colorless prismatic crystals. Melting point: 50°-51° C. (recrystallization solvent: ethyl acetate-n-hexane)

Workup

  1. customproviding Dean Stalk
  2. temperaturethe solution was refluxed for 10 hours
  3. temperatureunder heat
  4. distillationSolvent was distilled off under reduced pressure
  5. customthe residue was purified by means of silica gel column chromatography (development solvent: ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-ac7edbc04d0341afa2784b70da48b563
Source dataset
uspto-grants-1994_10
Patent number
US05359076

Reaction notes

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