Reacción #414724

Ecuación de reacción

(E)-2-[2-[3-[2-[4-(cyclobuty)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid

ethyl ether

diazomethane

→

(E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester

Disolventes

ethyl ether methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 10 min the excess of diazomethane was removed with a stream of nitrogen
2. 2
   Otrothe remaining solvents were removed in vacuo
3. 3
   LavadoThis solution was washed with water (2×15 ml)
4. 4
   Secadodried (MgSO4)
5. 5
   OtroRemoval of the volatiles
6. 6
   Otroin vacuo and recrystallization from ethyl acetate

Procedimiento

A suspension of 2.1 g of (E)-2-[2-[3-[2-[4-(cyclobuty)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid in 200 ml of ethyl ether/methylene chloride (1:3 v/v) was treated with an excess of an ethyl ether solution of diazomethane. After 10 min the excess of diazomethane was removed with a stream of nitrogen, the remaining solvents were removed in vacuo and the residual materials were taken up into methylene chloride. This solution was washed with water (2×15 ml) and dried (MgSO4). Removal of the volatiles in vacuo and recrystallization from ethyl acetate yielded 2.2 g of (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid methyl ester as an off-white solid, m.p. 143°-144° C. Anal. Calcd for C25H24N2O3S: C, 69.42; H, 5.59; N, 6.48. Found: C, 69.21; H, 5.63; N, 6.49.

Fuente