6-Chloronicotinoyl Chloride → HCID 56766827, compound

HRID 2199599Notes

Reaction equation

HRID 2199599 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](Cl)=[O:9])=[CH:4][CH:3]=1.O[NH:12][C:13](=[NH:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[C:14]([C:13]1[N:18]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=2)[O:9][N:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 178446865HCID 178446865, compound

Product 1

HCID 56766827HCID 56766827, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3.8 g (21.5 mmol) of 6-chloropyridine-3-carbonyl chloride in 100 mL of toluene, in Dean-stark apparatus, are added portionwise 2.5 g (21.5 mmol) N-hydroxy-2,2-dimethylpropanimidamide, and the reaction medium is stirred for 2 hours at room temperature and then heated for 2 hours. After cooling to room temperature, the medium is concentrated under reduced pressure and purified by chromatography on silica gel, eluting with a cyclohexane/EtOAc gradient of from 0 to 10% EtOAc. 4.1 g of 5-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-2-chloropyridine are obtained in the form of a white solid.

Workup

  1. temperatureheated for 2 hours
  2. temperatureAfter cooling to room temperature
  3. concentrationthe medium is concentrated under reduced pressure
  4. custompurified by chromatography on silica gel
  5. washeluting with a cyclohexane/EtOAc gradient of from 0 to 10% EtOAc

Sources & evidence

ORD record
ord-0de5d1af51ce45d48880721d2d5a63c1
Source dataset
uspto-grants-2016_06
Patent number
US09359329B2

Reaction notes

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