Thionyl Chloride → 6-Cyanonaphthalene-2-carbonyl chloride

HRID 232819Notes

Reaction equation

HRID 232819 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](O)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14]([NH2:16])=O.S(Cl)([Cl:19])=O>CN(C)C=O>[C:14]([C:2]1[CH:1]=[C:10]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[C:7]([C:11]([Cl:19])=[O:12])[CH:8]=[CH:9]2)#[N:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 211863766-(Aminocarbonyl)-2-naphthalenecarboxylic acid

Product 1

HCID 124330916-Cyanonaphthalene-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

2.8 g of naphthalene-2,6-dicarboxylic acid monoamide, 10 ml of thionylchloride and 1 drop of dimethylformamide are refluxed for 5 hours. The clear yellow solution is evaporated down in vacuo and the solid evaporation residue is mixed with 20 ml of diethylether and 20 ml of petroleum ether, then stirred and suction filtered. The filter cake is washed with petroleum ether and diethylether and dried in vacuo.

Workup

  1. customThe clear yellow solution is evaporated down in vacuo
  2. customthe solid evaporation residue
  3. additionis mixed with 20 ml of diethylether and 20 ml of petroleum ether
  4. filtrationsuction filtered
  5. washThe filter cake is washed with petroleum ether and diethylether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-05781eaca28f4b77ae0a4076659dc5f8
Source dataset
uspto-grants-1997_01
Patent number
US05591769

Reaction notes

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