반응 #63830

반응 방정식

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

용매

water

water

acetic acid

반응 조건

후처리

1. 1
   온도cooled
2. 2
   workup.ADDITIONis added dropwise, during a 15 minutes period
3. 3
   기타at about 10° C
4. 4
   workup.STIRRINGUpon completion, the whole is stirred for 60 minutes
5. 5
   workup.STIRRINGstirring
6. 6
   여과The product is filtered off
7. 7
   세척washed with water
8. 8
   workup.DISSOLUTIONdissolved in a mixture of trichloromethane and methanol (90:10 by volume)
9. 9
   기타The organic layer is dried
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타The 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
    기타The pure fractions are collected
15. 15
    기타the eluent is evaporated in vacuo

실험 절차

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.

출처