Dimethylformamide → 3-Chloro-3-phenyl-2-propenenitrile

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[CH3:7].C[N:16]([CH3:19])C=O>>[Cl:3][C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:7][C:19]#[N:16]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 7410Acetophenone

HCID 24813Phosphorus oxychloride

Product 1

HCID 27775113-Chloro-3-phenyl-2-propenenitrileYield 53%

Procedure

The reaction of dimethylformamide, phosphorous oxychloride and acetophenone as described earlier gave the product as an oil (0.72 g, 53%). 1H NMR (400 MHz, CDCl3): δ 7.64-7.67 (2H, m), 7.43-7.53 (3H, m), 6.02 (1H, s).

Sources & evidence

ORD record: ord-30c8233de55c4d9083a42482ce25a0e8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815879B2

Reaction notes

Loading…