Acetic Acid → HCID 21391803, compound

HRID 1439591Notes

Reaction equation

HRID 1439591 reaction equation
[Cl:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1CC#N.[C:18]([OH:21])(=[O:20])[CH3:19].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[C:7]([C:8](=[O:14])[C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:19][C:18]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 21391785HCID 21391785, compound

Product 1

HCID 21391803HCID 21391803, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.2 parts of 2-[2-chloro-3-(2-thenoyl)phenyl]acetonitrile, 7 parts of acetic acid, 7 parts of water and 12 parts of sulfuric acid is stirred and boiled for 1h.30. The reaction mixture is cooled, poured onto water and extracted with ether. The extract is washed with water, extracted with 50 parts of a 5% sodium hydroxide solution and the alkaline solution is washed with ether. After acidification with diluted hydrochloric acid solution, the whole is extracted again with ether. The extract is washed with water, treated with charcoal, filtered and evaporated. The residue is purified by column-chromatography over silicagel, using a mixture of chloroform and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 2-[2-chloro-3-(2-thenoyl)phenyl]acetic acid; mp. 112.2° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured onto water
  3. extractionextracted with ether
  4. washThe extract is washed with water
  5. extractionextracted with 50 parts of a 5% sodium hydroxide solution
  6. washthe alkaline solution is washed with ether
  7. extractionAfter acidification with diluted hydrochloric acid solution, the whole is extracted again with ether
  8. washThe extract is washed with water
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by column-chromatography over silicagel
  13. additiona mixture of chloroform and 5% of methanol as eluent
  14. customThe pure fractions are collected
  15. customthe eluent is evaporated

Sources & evidence

ORD record
ord-312fd709900f4baebcdb474799051219
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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