Thionyl Chloride → 6-Cyanonaphthalene-2-carbonyl chloride

HRID 325064Notes

Reaction equation

HRID 325064 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([OH:15])=O)[CH:7]=[CH:6]2)#[N:2].S(Cl)([Cl:18])=O.S([O-])([O-])(=O)=O.[Ca+2]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([Cl:18])=[O:15])[CH:7]=[CH:6]2)#[N:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24497Calcium SulfateHCID 124330906-Cyanonaphthalene-2-carboxylic acid

Product 1

HCID 124330916-Cyanonaphthalene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 6-cyano-naphthalene-2-carboxylic acid (250.00 mg, 1.27 mmol), thionyl chloride (15 mL), and a few drops of DMF was refluxed for two hours under a condenser equipped with a drying tube containing anhydrous calcium sulfate. The thionyl chloride was then removed by high vacuum distillation, yielding a quantitative yield of a yellow solid. This material was not characterized, and was carried on without further purification.

Workup

  1. temperaturewas refluxed for two hours under a condenser
  2. customequipped with a drying tube
  3. customThe thionyl chloride was then removed by high vacuum distillation

Sources & evidence

ORD record
ord-aca9966e54ec44b29a6523fcf589028a
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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