Triethylamine → 2-(4-Methylphenoxy)-2-(2'-chlorophenyl)acetonitrile

Reaction equation

[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]([NH2:10])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]#[N:10])=[CH:18][CH:19]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 24813Phosphorus oxychloride

HCID 193855922-(4-Methylphenoxy)-2-(2-chlorophenyl)acetamide

Product 1

HCID 193856812-(4-Methylphenoxy)-2-(2'-chlorophenyl)acetonitrileYield 91.3%

Procedure

The product of Step A (0.650 g, 2.36 mmol) was added to phosphorous oxychloride (5.95 mL, 27 eq) at 0° C. followed by slow addition of 0.73 mL (2.2 eq) of triethylamine. The reaction mixture was warmed to room temperature for 10 minutes, refluxed for 50 minutes and then cooled to room temperature. The reaction mixture was concentrated in vacuo, and partitioned between ice water and toluene. The aqueous layer was extracted 3 times with toluene, and the combined toluene extracts were washed with 0.5N NaOH and H2O. The crude product was concentrated in vacuo and purified on a silica gel flash chromatography column (140×30 mm) eluted with 2% ethyl acetate/hexane to afford 0.555 g (91%) of the title compound.