Pyridine → Benzoic acid, 2-(2-naphthalenylthio)-

HRID 616353Notes

Reaction equation

HRID 616353 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[SH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>O>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[S:11][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 69412-Iodobenzoic acidHCID 70582-NaphthalenethiolHCID 11430Potassium Carbonate

Product 1

HCID 12228096Benzoic acid, 2-(2-naphthalenylthio)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A well stirred mixture of 37.2 g. (0.15 mole) of o-iodobenzoic acid, 34.0 g. (0.15 mole) of 2-mercaptonaphthalene, 20.6 g. (0.15 mole) of potassium carbonate and 300 ml. of pyridine is heated at 50° C. for 1 hour, then 5 g. of cuprous chloride is added and the stirred mixture is heated at reflux for 18 hours. The mixture is poured into 1.2 liters of water and filtered. The filtrate is acidified and the resulting mixture is extracted into methylene chloride. The extracts are dried, concentrated, and the solid residue is recrystallized to give 2-(2-naphthylthio)benzoic acid.

Workup

  1. additionmixture of 37.2 g
  2. temperaturethe stirred mixture is heated
  3. temperatureat reflux for 18 hours
  4. filtrationfiltered
  5. extractionthe resulting mixture is extracted into methylene chloride
  6. customThe extracts are dried
  7. concentrationconcentrated
  8. customthe solid residue is recrystallized

Sources & evidence

ORD record
ord-790e922d1c994de495aaa4e1d41b6c16
Source dataset
uspto-grants-1978_02
Patent number
US04073912

Reaction notes

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