p-Chlorothiophenol → 5-(4-Chlorophenylthio)furan-3-carboxylic Acid

HRID 894245Notes

Reaction equation

HRID 894245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:10]2[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7815p-ChlorothiophenolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 211624635-(4-Chlorophenylthio)furan-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Chlorothiophenol (4.52 g., 31.4 mmoles) was reacted with 5-bromo-furan-3-carboxylic acid according to the procedure of Example 15, except that the total volume of dimethylformamide was 85 ml., and the reflux period was 8 hours. The reaction mixture was cooled, filtered, the filtrate diluted with 500 ml. of water and insolubles removed by filtration. The latter filtrate was made acidic with 6 N hydrochloric acid, product was extracted into ethyl acetate and recovered by evaporation to an oil, crystallized by trituration with water (860 mg.). Two crystallizations from methanol/water gave purified 5-(4-chlorophenylthio)furan-3-carboxylic acid (150 mg., m.p. 142°-145° C., m/e 254). Analysis: Calcd. for C11H7O3SCl; C, 51.87; H, 2.77. Found: C, 51.97; H, 2.99.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionthe filtrate diluted with 500 ml
  4. customof water and insolubles removed by filtration
  5. extractionwas extracted into ethyl acetate
  6. customrecovered by evaporation to an oil
  7. customcrystallized by trituration with water (860 mg.)
  8. customTwo crystallizations from methanol/water
  9. customgave
  10. custompurified 5-(4-chlorophenylthio)furan-3-carboxylic acid (150 mg., m.p. 142°-145° C., m/e 254)

Sources & evidence

ORD record
ord-d1aa296233aa489ca561abff87a66a91
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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