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

HRID 355361Notes

Reaction equation

HRID 355361 reaction equation
C([O:3][C:4](=O)[NH:5][C:6](=[O:30])[C:7](=[N:10][NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([CH:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:20]#[N:21])=[C:14]([Cl:29])[CH:13]=1)[C:8]#[N:9])C.C([O-])(=O)C.[K+]>C(O)(=O)C>[Cl:29][C:14]1[CH:13]=[C:12]([N:11]2[C:4](=[O:3])[NH:5][C:6](=[O:30])[C:7]([C:8]#[N:9])=[N:10]2)[CH:17]=[C:16]([Cl:18])[C:15]=1[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:20]#[N:21]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 131720911HCID 131720911, compound2×

Product 1

HCID 189421712-[3,5-Dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-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 7.8 parts of ethyl[2-[[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]hydrazono]-2-cyanoacetyl]carbamate (intermediate 3), 1.98 parts of anhydrous potassium acetate and 120 parts of acetic acid is stirred and heated under reflux for 3 hours. The reaction mixture is concentrated to a volume of 30 parts. Water is added until the product is precipitated. It is sucked off, washed with water and dissolved in trichloromethane. The remaining water is separated and the organic phase is dried, filtered and evaporated, yielding 2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile (intermediate 4).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture is concentrated to a volume of 30 parts
  4. additionWater is added until the product
  5. customis precipitated
  6. washwashed with water
  7. dissolutiondissolved in trichloromethane
  8. customThe remaining water is separated
  9. customthe organic phase is dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-4f04aa85a2f24b8aad9342e20a01596f
Source dataset
uspto-grants-1998_11
Patent number
US05830893

Reaction notes

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