Pyridine → HCID 57468510, compound

HRID 656501Notes

Reaction equation

HRID 656501 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([I:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])#[N:2].S(Cl)(Cl)=O.[C:17](O)([CH3:20])([CH3:19])[CH3:18].N1C=CC=CC=1>CN(C)C=O.C(Cl)(Cl)Cl>[C:17]([O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=1[I:12])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 24386Thionyl ChlorideHCID 220088225-Cyano-2-iodobenzoic acid

Product 1

HCID 57468510HCID 57468510, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

8.9 mmol of 5-Cyano-2-iodo-benzoic acid [219841-92-6] is heated at reflux with 6 ml of thionyl-chloride and 1 drop of N,N-dimethylformamide until all the solid dissolves and there is no further gas evolution. The solution is cooled to room temperature and evaporated to dryness. The residue is treated with 32 mmol of dry tert-butyl alcohol and 49 mmol of dry pyridine in 5 ml of chloroform at 0° C. under an Ar atmosphere. After the addition, the mixture is refluxed overnight, cooled, and evaporated to dryness. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. dissolutiondissolves
  2. customevaporated to dryness
  3. additionAfter the addition
  4. temperaturethe mixture is refluxed overnight
  5. temperaturecooled
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-94e58acd2a8a423bbb00b04ee58ab219
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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