Reacción #2467971

Ecuación de reacción

sodium methoxide

methyl thioglycolate

sodium methoxide

3-chloro-3-phenylprop-2-enenitrile

water

→

solid

Rendimiento 62.9%

Methyl 3-amino-5-phenylthiophene-2-carboxylate

Rendimiento 62.9%

Disolventes

methanol

methanol

methanol

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred the mixture at 60° C. for 2 h
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 2 h at 60° C
4. 4
   Otrowas allowed to rt
5. 5
   workup.STIRRINGstirred for 15 min
6. 6
   ExtracciónThe solution was extracted with chloroform (3×100 mL)
7. 7
   Lavadothe combined chloroform layer was washed with water, brine
8. 8
   Secadodried over sodium sulfate
9. 9
   FiltraciónThe solution was filtered
10. 10
    Otroevaporated the solvent
11. 11
    OtroThe residue was chromatographed over silica gel

Procedimiento

To a solution of methyl thioglycolate (1 g, 9.43 mmol) in methanol (5 mL) was added a solution of sodium methoxide (0.5 g, 9.43 mmol) in methanol (5 mL) and stirred for 0.5 h. To the above mixture, a solution of 3-chloro-3-phenylprop-2-enenitrile (1.22 g, 7.5 mmol) in DMF (3.5 mL) was added dropwise for 10 min at rt and stirred the mixture at 60° C. for 2 h. Then, a solution of sodium methoxide (1 g, 18.6 mmol) in methanol (10 mL) was added dropwise at rt and stirring was continued for 2 h at 60° C. The mixture was allowed to rt and poured into cold water and stirred for 15 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel using hexane-ethyl acetate (92:8) as eluent to give the product as a pale yellow color solid (1.1 g, 50%), mp 130-132° C. 1H NMR (400 MHz, DMSO-d6): δ 7.62-7.65 (2H, m), 7.38-7.48 (3H, m), 7.00 (1H, s), 4.29 (2H, br s), 3.74 (3H, s); LC-MS (positive ion mode): m/z 234 (M+H)+.

Fuente