4-Chloropyridine hydrochloride → HCID 21700231, compound

HRID 1978030Notes

Reaction equation

HRID 1978030 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 818524-Chloropyridine hydrochlorideHCID 1233504-(Methylsulfonyl)phenol

Product 1

HCID 21700231HCID 21700231, compoundYield 19.1%

Conditions

Temperature
150 °C

Procedure

A mixture of 4-methylsulfonylphenol (2.93 g, 17 mmol) and 4-chloropyridine hydrochloride (2.93 g, 19.5 mmol) was heated at 150° C., resulting in a gradual melt, which was stirred at 150° C. for 4 hours, then partitioned between ethyl acetate and 1N NaOH. The organic extract was dried over MgSO4, filtered, and concentrated to 1.3 g of a yellow solid. The solid was recrystallized from ethyl acetate-ether to give 0.81 g of the desired product as a white solid.

Workup

  1. customresulting in a gradual melt, which
  2. custompartitioned between ethyl acetate and 1N NaOH
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to 1.3 g of a yellow solid
  7. customThe solid was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-56446c7123474ec5b87aff3c7d9b5b7e
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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