Thionyl Chloride → 2-Chloronicotinoyl chloride

HRID 2350857Notes

Reaction equation

HRID 2350857 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[C:7]([C:8]([Cl:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acid

Product 1

HCID 27745412-Chloronicotinoyl chlorideYield 99%

Procedure

A mixture of 50.0 g (0.317 mole) of 2-chloropyridine-3-carboxylic acid and 120 ml of thionyl chloride was heated at reflux for 3 hours. The resulting solution was concentrated to dryness. The resulting oil was diluted twice with methylene chloride and concentrated to dryness to give 55.4 g of 2-chloropyridine-3-carbonyl chloride. Total yield 99%. This acid chloride was added to a mixture of 76.9 g (0.315 mole) of 2-methylthio-2-imidazoline hydrochloride, 1 liter of methylene chloride, and 63.7 g (0.630 mole) of triethylamine. This mixture was heated at reflux for 16 hours. The resulting solvent was removed by evaporation and the residue was stirred with water for 15 minutes. A white solid was collected by filtration and dried to give 69.2 g of 1-(2-chloropyridine-3-carbonyl)-2-methylthio-2-imidazoline; melting point 100°-102° C. Total yield 86%. This compound exhibits the following formula ##STR8##

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe resulting solution was concentrated to dryness
  4. additionThe resulting oil was diluted twice with methylene chloride
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-005b3794fdf3452d991e8719dc3fecb4
Source dataset
uspto-grants-1989_10
Patent number
US04871732

Reaction notes

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