Phosphorus oxychloride → HCID 14885582, compound

HRID 542766Notes

Reaction equation

HRID 542766 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[C:12]([C:17]([NH:19]C(C)(C)C)=O)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[C:12]([C:17]#[N:19])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14885575HCID 14885575, compound

Product 1

HCID 14885582HCID 14885582, compoundYield 91.6%

Procedure

A solution of 3-[2-(3,4-dichlorophenyl)ethyl]-N-(1,1-dimethylethyl)-2-pyridine carboxamide (37.8 g, 0.107 mole) in 120 mL (197.4 g, 1.29 mole) of phosphorous oxychloride is heated at 110° C. for 4.5 hours. Completion of the reaction is determined by thin-layer chromotography. The reaction is quenched with ice and H2O and the pH of the solution is brought to 8 by the addition of a saturated solution of potassium carbonate. The product is extracted into ethylacetate. The solution is concentrated to a solid residue which upon recrystallization from diethyl ether/ethyl acetate provides the desired product, (27.1 g, 0.098 mole), in 91.6% yield.

Workup

  1. customThe reaction is quenched with ice and H2O
  2. additionthe pH of the solution is brought to 8 by the addition of a saturated solution of potassium carbonate
  3. extractionThe product is extracted into ethylacetate
  4. concentrationThe solution is concentrated to a solid residue which upon recrystallization from diethyl ether/ethyl acetate

Sources & evidence

ORD record
ord-b0eb0507eb294802a1a68eb4fc44eb35
Source dataset
uspto-grants-1987_04
Patent number
US04659716

Reaction notes

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