Sulfuric Acid → HCID 11674351, compound

HRID 2299217Notes

Reaction equation

HRID 2299217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22]C)=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].S(=O)(=O)(O)O>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 9928140ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate2×

Product 1

HCID 11674351HCID 11674351, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 3, 300 mg) obtained in Example 3 in methanol (6 ml), concentrated sulfuric acid (0.4 ml) was added and the mixture was stirred under reflux for 8 days. The reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate (30 ml) and washed with water (30 ml). The ethyl acetate layer was washed with water (30 ml×2) and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/5→ethyl acetate/hexane=1/2) and then crystallized from diisopropyl ether to yield methyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 22; 95 mg) as colorless powdery crystals.

Workup

  1. temperatureunder reflux for 8 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate (30 ml)
  4. washwashed with water (30 ml)
  5. washThe ethyl acetate layer was washed with water (30 ml×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/5→ethyl acetate/hexane=1/2)
  9. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7b339742977640ca9581ada9f4f1a50e
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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