Acetic Acid → HCID 16640236, compound

HRID 1723167Notes

Reaction equation

HRID 1723167 reaction equation
[N+:1]([C:4]1[S:5][C:6]([Cl:10])=[C:7]([Cl:9])[CH:8]=1)([O-])=O.[C:11](O)(=[O:13])[CH3:12].C(OC(=O)C)(=O)C.Cl>[Fe].O>[Cl:9][C:7]1[CH:8]=[C:4]([NH:1][C:11](=[O:13])[CH3:12])[S:5][C:6]=1[Cl:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 20026753HCID 20026753, compound

Product 1

HCID 16640236HCID 16640236, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a cooled solution of the above 4,5-dichlorothiophene (13.0 g, 66.0 mmol) are added acetic acid (78 ml) and acetic anhydride (78 ml), followed by iron powder (13.0 g) in portions over 30 min. at such rate that the mixture is kept at 5°-10°. The suspension is stirred at RT overnight, after which it is poured into water, acidified with conc. HCl and cooled in an ice bath for 6 hours. It is then filtered, and the solid is washed with water and dried, dissolved in ether and filtered. Charcoal is added to the filtrate, which is then filterded and stripped of solvent to give N-(4,5-dichloro-2-thienyl)acetamide, a solid.

Workup

  1. customis kept at 5°-10°
  2. temperaturecooled in an ice bath for 6 hours
  3. filtrationIt is then filtered
  4. washthe solid is washed with water
  5. customdried
  6. dissolutiondissolved in ether
  7. filtrationfiltered
  8. additionCharcoal is added to the filtrate, which

Sources & evidence

ORD record
ord-42732d4643784aadad3609ca3782ab0c
Source dataset
uspto-grants-1989_08
Patent number
US04859699

Reaction notes

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