3-Methoxyaniline → n-(3-Methoxyphenyl)-3-oxo-3-(1,3-thiazol-2-yl)propaneamide

HRID 39711

Reaction equation

HRID 39711 reaction equation
[O:1]=[C:2]([C:8]1[S:9][CH:10]=[CH:11][N:12]=1)[CH2:3][C:4]([O:6]C)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1>C1(C)C(C)=CC=CC=1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:21][C:4](=[O:6])[CH2:3][C:2](=[O:1])[C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 57436906Methyl 3-oxo-3-(1,3-thiazol-2-yl)propanoate

Product 1

HCID 59397932n-(3-Methoxyphenyl)-3-oxo-3-(1,3-thiazol-2-yl)propaneamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 30 mL of a xylene solution containing 2.3 g of methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate, 1.4 mL of m-anisidine was added. The reaction mixture was stirred for 6 hours under reflux by heating. The solvent was removed under reduced pressure, and water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 3.3 g of a brown oily substance, N-(3-methoxyphenyl)-3-oxo-3-(1,3-thiazol-2-yl)propaneamide.

Workup

  1. additionwas added
  2. temperatureunder reflux
  3. temperatureby heating
  4. customThe solvent was removed under reduced pressure, and water and ethyl acetate
  5. additionwere added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-550d0306c7964def8c9e5963eb868381
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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