Dimethylformamide dimethyl acetal → 3-[3-(Dimethylamino)prop-2-enoyl]benzonitrile

HRID 968682Notes

Reaction equation

HRID 968682 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>ClCCl>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])=[O:3]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 802223-Acetylbenzonitrile

Product 1

HCID 28062053-[3-(Dimethylamino)prop-2-enoyl]benzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-Acetyl-benzonitrile (36.2 g, 249 mmol) in dimethylformamide dimethylacetal (200 mL, excess) was heated to reflux overnight. The solvent was evaporated in vacuo to afford an orange solid. The solid was dissolved in dichloromethane and filtered over a plug of silica gel eluting with 20% ethyl acetate/dichloromethane. The filtrate was concentrated in vacuo to afford 42.0 g (84%) of the title compound as an orange solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated in vacuo
  4. customto afford an orange solid
  5. filtrationfiltered over a plug of silica gel eluting with 20% ethyl acetate/dichloromethane
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8461d3193bd14234bdd3c46063ece7d4
Source dataset
uspto-grants-2007_12
Patent number
US07304071B2

Reaction notes

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