Triethylamine → HCID 53996767, compound

HRID 255955

Reaction equation

HRID 255955 reaction equation
[CH3:1][N:2]([CH3:7])[CH:3]=[CH:4][C:5]#[N:6].C(N(CC)CC)C.[Cl:15][C:16]1[CH:24]=[C:23]([Cl:25])[C:22]([F:26])=[CH:21][C:17]=1[C:18](Cl)=[O:19]>O1CCOCC1>[CH3:1][N:2]([CH3:7])[CH:3]=[C:4]([C:18](=[O:19])[C:17]1[CH:21]=[C:22]([F:26])[C:23]([Cl:25])=[CH:24][C:16]=1[Cl:15])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 974973-(Dimethylamino)prop-2-enenitrileHCID 27368212,4-Dichloro-5-fluorobenzoyl chloride

Product 1

HCID 53996767HCID 53996767, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9.6 g of 3-dimethylaminoacrylonitrile and 10.5 g of triethylamine are added dropwise to a solution of 22.75 g of 2,4-dichloro-5-fluorobenzoyl chloride in 100 ml of anhydrous dioxane, while cooling in ice and stirring. The mixture is stirred at room temperature for 1 hour and then heated to boiling under reflux for 4 hours. The solvent is removed by distillation in vacuo, and the residue is taken up in methylene chloride/water. The methylene chloride phase is washed with water, dried with sodium sulphate, and evaporated in vacuo. The crystalline residue is recrystallized from ethanol. 22.2 g of 3-dimethylamino-2-(2,4-dichloro-5-fluorobenzoyl)acrylonitrile of melting point 138°-139° C. are obtained.

Workup

  1. temperaturewhile cooling in ice
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. temperatureheated
  4. temperatureunder reflux for 4 hours
  5. customThe solvent is removed by distillation in vacuo
  6. washThe methylene chloride phase is washed with water
  7. dry with materialdried with sodium sulphate
  8. customevaporated in vacuo
  9. customThe crystalline residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-79dc08f483de46299a7c81bb61a53f4d
Source dataset
uspto-grants-1987_10
Patent number
US04699992

Linked notes

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