Potassium Nitrate → 7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluoro-2-nitro-phenyl)-ethyl]-methyl-amide

HRID 1351270Notes

Reaction equation

HRID 1351270 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[N+:25]([O-])([O-:27])=[O:26].[K+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[C:4]([N+:25]([O-:27])=[O:26])[CH:3]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 866009897-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide

Product 1

HCID 210986797-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluoro-2-nitro-phenyl)-ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-ethyl]-methyl-amide (the compound of Preparation Example 41) (222 mg) was dissolved in a concentrated sulfuric acid (1.5 mL), potassium nitrate (74 mg) was added in small amounts on an ice bath. After stirring for 45 minutes, the reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium bicarbonate and saturated sodium chloride water, and dried with anhydrous magnesium sulfate. Spots for two products were identified by silica gel TLC (hexane/ethyl acetate=1:1). The residue resulting from the removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), fractions with a high RF value were collected, and the title compound (78 mg) was obtained as a colorless solid.

Workup

  1. additionwas added in small amounts on an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of sodium bicarbonate and saturated sodium chloride water, and dried with anhydrous magnesium sulfate
  5. customThe residue resulting from the removal of the solvent by evaporation
  6. customwas purified by silica gel column chromatography (hexane/ethyl acetate), fractions with a high RF value
  7. customwere collected

Sources & evidence

ORD record
ord-9b6e4481f286467a82303184ef084e2e
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

Loading…