Thionyl Chloride → 2-Chloronicotinoyl chloride

HRID 1976533Notes

Reaction equation

S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9]>>[Cl:5][C:6]1[C:7]([C:8]([Cl:3])=[O:9])=[CH:11][CH:12]=[CH:13][N:14]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride2×

HCID 762582-Chloronicotinic acid

Product 1

HCID 27745412-Chloronicotinoyl chlorideYield 100.6%

Conditions

Temperature: 90 °C

Procedure

1131 g (9.5 mol) of thionyl chloride were slowly added dropwise at 90° C. to 500 g (3.17 mol) of 2-chloronicotinic acid. The reaction mixture was stirred for 1 hour at 90° C. and freed from thionyl chloride under reduced pressure (“high vacuum”) at approximately 40° C. This gave 561 g (100%) of the title compound as colorless crystals.

Sources & evidence

ORD record: ord-66af3623d69f4f39b65bd25a25ba35a9
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06228810B1

Reaction notes

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