Hydrochloric Acid → n-(3,4-Dimethyl-5-isoxazolyl)-5-phenylthiophen-2-sulfonamide

HRID 2270591Notes

Reaction equation

HRID 2270591 reaction equation
Cl.COCCOC[N:8]([C:23]1[O:27][N:26]=[C:25]([CH3:28])[C:24]=1[CH3:29])[S:9]([C:12]1[S:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)(=[O:11])=[O:10]>C(O)C>[CH3:28][C:25]1[C:24]([CH3:29])=[C:23]([NH:8][S:9]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][CH:16]=2)(=[O:11])=[O:10])[O:27][N:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53733365N-(Methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-phenylthiophene-2-sulfonamide

Product 1

HCID 23445540n-(3,4-Dimethyl-5-isoxazolyl)-5-phenylthiophen-2-sulfonamideYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

HCl (3 ml of a 3 N aqueous solution) was added to a solution of N-(methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-phenylthiophene-2-sulfonamide (100 mg, 0.24 mmol) in 3 ml of 95% ethanol and the resulting mixture was refluxed for 6 h. The mixture was then concentrated, diluted with 5 ml of water, neutralized with saturated aqueous sodium bicarbonate solution and acidified to pH 4 using glacial acetic acid. The mixture was extracted with ethyl acetate (2×25 ml) and the combined organic extract was washed with brine (1×5 ml), dried and evaporated. Flash chromatography of the residue on silica gel using 2% MeOH/CHCl3 and further purification by reverse phase HPLC yielded 33.4 mg (42%) of the pure sulfonamide as a white powder, m.p. 176-178° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 h
  2. concentrationThe mixture was then concentrated
  3. additiondiluted with 5 ml of water
  4. extractionThe mixture was extracted with ethyl acetate (2×25 ml)
  5. extractionthe combined organic extract
  6. washwas washed with brine (1×5 ml)
  7. customdried
  8. customevaporated
  9. customFlash chromatography of the residue on silica gel using 2% MeOH/CHCl3 and further purification by reverse phase HPLC

Sources & evidence

ORD record
ord-bf85e68998f24ecaa3ac25280186e7e9
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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