Potassium Acetate → 2-[4-[(4-Chlorophenyl)cyanomethyl]-3-methoxyphenyl]2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

HRID 1710027Notes

Reaction equation

HRID 1710027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]#[N:31])[C:9]2[CH:14]=[CH:13][C:12]([NH:15][N:16]=[C:17]([C:26]#[N:27])[C:18]([NH:20][C:21](=O)[O:22]CC)=[O:19])=[CH:11][C:10]=2[O:28][CH3:29])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:30]#[N:31])[C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:21](=[O:22])[NH:20][C:18](=[O:19])[C:17]([C:26]#[N:27])=[N:16]3)=[CH:11][C:10]=2[O:28][CH3:29])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 86742407Ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate

Product 1

HCID 230351972-[4-[(4-Chlorophenyl)cyanomethyl]-3-methoxyphenyl]2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture is evaporated in vacuo
  3. stirringThe residue is stirred in water
  4. filtrationThe product is filtered off
  5. dissolutiondissolved in trichloromethane
  6. customThe organic layer is dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  11. customThe pure fractions are collected
  12. customthe eluent is evaporated in vacuo

Sources & evidence

ORD record
ord-1d780a640ab74f9c862f9151602cf3cc
Source dataset
uspto-grants-1990_08
Patent number
US04952570

Reaction notes

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