Thionyl Chloride → 5-Cyano-2,3-dihydro-3,3-dimethylbenzofuran

HRID 444097Notes

Reaction equation

HRID 444097 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[C:8]([C:11]([NH2:13])=O)[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.S(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[C:8]([C:11]#[N:13])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 540896312,3-Dihydro-3,3-dimethylbenzofuran-5-carboxylic acid amide

Product 1

HCID 205361905-Cyano-2,3-dihydro-3,3-dimethylbenzofuran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product of stage (c) was boiled under reflux in benzene (5 ml) with thionyl chloride for 6 hours. Washing with water, drying over magnesium sulphate and running down gave, after recrystallisation from petroleum ether (bp 60°-80° C.), 0.6 g of title product, mp 70°-72° C.

Workup

  1. washWashing with water
  2. dry with materialdrying over magnesium sulphate
  3. customrunning down gave
  4. customafter recrystallisation from petroleum ether (bp 60°-80° C.), 0.6 g of title product, mp 70°-72° C.

Sources & evidence

ORD record
ord-9b522b5ee6034ceea67b7cfa97d97125
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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