Reaction #63831

Reaction equation

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

potassium acetate

→

2-[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperatureat reflux temperature
2. 2
   OtherThe reaction mixture is evaporated in vacuo
3. 3
   workup.STIRRINGThe residue is stirred in water
4. 4
   FiltrationThe product is filtered off
5. 5
   workup.DISSOLUTIONdissolved in trichloromethane
6. 6
   OtherThe organic layer is dried
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated
9. 9
   OtherThe residue is purified by column chromatography over silica gel using
10. 10
    workup.ADDITIONa mixture of trichloromethane and methanol (90:10 by volume) as eluent
11. 11
    OtherThe pure fractions are collected
12. 12
    Otherthe eluent is evaporated in vacuo

Procedure

A mixture of 8.3 parts of ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate, 1.77 parts of anhydrous potassium acetate and 100 parts of acetic acid is stirred for 2 hours at reflux temperature. The reaction mixture is evaporated in vacuo. The residue is stirred in water. The product is filtered off and dissolved in trichloromethane. 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 (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo, yielding 2-[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile.

Source