Thionyl Chloride → 3,5-Dichloropyridine-4-carbon chloride

HRID 23888

Reaction equation

HRID 23888 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8](O)=[O:9].S(Cl)([Cl:14])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C:8]([Cl:14])=[O:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 6057633,5-Dichloroisonicotinic acid

Product 1

HCID 115720223,5-Dichloropyridine-4-carbon chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3,5-Dichloropyridine-4-carboxylic acid (0.5 g, 2.6 mmol; Reference Example 1) was dissolved in CH2Cl2 (1.75 mL) and DMF (50 μL). Thionyl chloride (0.21 mL, 2.86 mL) was added and the reaction mixture was heated at 50° C. for 20 h. The residue was concentrated in vacuo. The formation of the acid chloride was observed by TLC (50% EtOAc/hexane) and the crude 3,5-dichloropyridine-4-carboxylic acid chloride was used in Step E without further purification.

Workup

  1. concentrationThe residue was concentrated in vacuo
  2. customthe crude 3,5-dichloropyridine-4-carboxylic acid chloride was used in Step E without further purification

Sources & evidence

ORD record
ord-82bcd2e31e4742e288da7ae9c3316792
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Linked notes

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