Dimethylformamide → 5,6-dichloropyridine-3-carbonyl Chloride

HRID 1942262Notes

Reaction equation

HRID 1942262 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].CN(C)C=O.S(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:19])=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 2479875,6-Dichloronicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 27821565,6-dichloropyridine-3-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a well stirred suspension of 5,6-dichloronicotinic acid 11 (600 g, 3.125 mole) and N,N-dimethylformamide (20.0 mL) in dichloroethane (1.2 L) was added drop wise with stirring thionyl chloride (743.56 g, 6.25 mole). The reaction mixture was set up for heating with reflux, fitted with a gas trap filled with saturated aqueous sodium bicarbonate and heated at 75° C. until the reaction mixture formed a clear solution, about 3 h. LC/MS of a sample quenched in methanol showed only methyl ester. The reaction mixture was cooled to ambient and concentrated under reduced pressure to yield 5,6-dichloronicotinoyl chloride 12 as a thick paste.

Workup

  1. temperaturefor heating
  2. temperaturewith reflux
  3. customfitted with a gas trap
  4. customformed a clear solution, about 3 h
  5. customLC/MS of a sample quenched in methanol
  6. temperatureThe reaction mixture was cooled to ambient and
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb1c06493e2f4b6ea6ac13e9f61cb363
Source dataset
uspto-grants-2013_03
Patent number
US08389549B2

Reaction notes

Loading…