Reacción #63830

Ecuación de reacción

4-amino-α-(4-chlorophenyl)-2-methoxybenzeneacetonitrile

hydrochloric acid

sodium acetate

ethyl (2-cyanoacetyl)carbamate

sodium nitrite

→

ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate

Disolventes

water

water

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   workup.ADDITIONis added dropwise, during a 15 minutes period
3. 3
   Otroat about 10° C
4. 4
   workup.STIRRINGUpon completion, the whole is stirred for 60 minutes
5. 5
   workup.STIRRINGstirring
6. 6
   FiltraciónThe product is filtered off
7. 7
   Lavadowashed with water
8. 8
   workup.DISSOLUTIONdissolved in a mixture of trichloromethane and methanol (90:10 by volume)
9. 9
   OtroThe organic layer is dried
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated
12. 12
    OtroThe residue is purified by column chromatography over silica gel using
13. 13
    workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
14. 14
    OtroThe pure fractions are collected
15. 15
    Otrothe eluent is evaporated in vacuo

Procedimiento

To a stirred and cooled (5°-10° C.) mixture of 5.6 parts of 4-amino-α-(4-chlorophenyl)-2-methoxybenzeneacetonitrile, 6.2 parts of concentrated hydrochloric acid and 50 parts of acetic acid is added dropwise, during a 15 minutes period, a solution of 1.25 parts of sodium nitrite in 10 parts of water at about 10° C. Upon completion, the whole is stirred for 60 minutes and then 3.6 parts of anhydrous sodium acetate and 2.8 parts of ethyl (2-cyanoacetyl)carbamate are added and stirring is continued for 2 hours at room temperature. The reaction mixture is poured into 250 parts of water. The product is filtered off, washed with water and dissolved in a mixture of trichloromethane and methanol (90:10 by volume). The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo, yielding ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate.

Fuente