Thionyl Chloride → (3-Methoxyphenyl)acetonitrile

HRID 35598

Reaction equation

HRID 35598 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([NH2:16])=O)[CH:10]=[CH:11][CH:12]=1>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:16])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27749732-(3-Methoxyphenyl)acetamide

Product 1

HCID 88310(3-Methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (1249 ml) was added dropwise to dry dimethylformamide (400 ml) stirring at 0°-5° C. under nitrogen over a period of about 2 hours. 3-Methoxyphenylacetamide (403.7 g) was added portionwise over a period of 45 minutes to the above solution under nitrogen maintaining the temperature between 0°-5° C. The reaction mixture was then stirred at 0°-5° C. for a further 2 hours. The reaction mixture was poured carefully onto ice/water (6 l). The aqueous mixture was extracted with ether. The extracts were washed with water, dried over magnesium sulphate and evaporated in vacuo to give a red liquid. The crude product was distilled (110°-112° C./12 mm Hg) to give 3-methoxyphenylacetonitrile.

Workup

  1. stirringThe reaction mixture was then stirred at 0°-5° C. for a further 2 hours
  2. additionThe reaction mixture was poured carefully onto ice/water (6 l)
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a red liquid
  8. distillationThe crude product was distilled (110°-112° C./12 mm Hg)

Sources & evidence

ORD record
ord-9c9dcda28fe244a7982077b1f6608d72
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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