Ammonium Hydroxide → 4-(4-Methoxybenzoyl)thiophene-2-sulfonamide

HRID 2072692Notes

Reaction equation

HRID 2072692 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:14](O)(=[O:16])=[O:15])[S:12][CH:13]=2)=[O:8])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[NH4+:24].[OH-]>C(Cl)Cl.CC(C)=O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:14]([NH2:24])(=[O:16])=[O:15])[S:12][CH:13]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 146390674-(4-Methoxybenzoyl)thiophene-2-sulfonic acid

Product 1

HCID 146390694-(4-Methoxybenzoyl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.98 g (0.01 mol) of product from Step B suspended in 75 ml CH2Cl2 was added excess thionyl chloride and the resulting suspension was stirred, and heated at reflux for 1.5 hours to give a homogeneous solution. The thionyl chloride was evaporated and the residue was extracted with CHCl3 after ice had been added. The organic extract was washed with brine, dried and the solvent evaporated to give a yellow oil. This was taken up in acetone and treated with 5 ml of concentrated NH4OH dropwise. After stirring for 15 minutes, this was extracted with chloroform and the extract was dried. Filtration and evaporation of the solvent gave the desired product as a yellow solid, m.p. 173°-175° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. customto give a homogeneous solution
  4. customThe thionyl chloride was evaporated
  5. extractionthe residue was extracted with CHCl3 after ice
  6. additionhad been added
  7. extractionThe organic extract
  8. washwas washed with brine
  9. customdried
  10. customthe solvent evaporated
  11. customto give a yellow oil
  12. stirringAfter stirring for 15 minutes
  13. extractionthis was extracted with chloroform
  14. customthe extract was dried
  15. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-2ac3e362dc4d42f38ee2385855534612
Source dataset
uspto-grants-1990_04
Patent number
US04914111

Reaction notes

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