Potassium Carbonate → HCID 16782287, compound

HRID 230792

Reaction equation

HRID 230792 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.Cl.Cl[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][S:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 957384-Mercaptobenzoic acid

Product 1

HCID 16782287HCID 16782287, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

An ethanol/water mixed solution (2/1, 60 mL) of 4-mercaptobenzenecarboxylic acid (1.0 g), 2-chloromethylpyridine hydrochloride (2.1 g) and potassium carbonate (4.5 g) was heated under reflux for 4 hours. The organic solvent was evaporated off under reduced pressure, and aqueous 5 N hydrochloric acid solution was added to the residue until it became acidic. Water was evaporated off under reduced pressure, and DMF was added to the resulting residue and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform/methanol=9/1 to 4/1) to obtain the entitled compound (650 mg).

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe organic solvent was evaporated off under reduced pressure, and aqueous 5 N hydrochloric acid solution
  3. additionwas added to the residue until it
  4. customWater was evaporated off under reduced pressure, and DMF
  5. additionwas added to the resulting residue
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (chloroform/methanol=9/1 to 4/1)

Sources & evidence

ORD record
ord-e616d6cef73c4db7ba90b40ae60674af
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Linked notes

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