1-Propanol → HCID 11544982, compound

HRID 2299218Notes

Reaction equation

HRID 2299218 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][CH3:23])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].S(=O)(=O)(O)O.[CH2:29](O)CC>>[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][CH2:23][CH3:29])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])=[O:12]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 9928140ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate2×

Product 1

HCID 11544982HCID 11544982, compound

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 1-propanol (6 ml), concentrated sulfuric acid (0.3 ml) was added and the mixture was stirred under reflux for 50 hours. 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 subjected to silica gel chromatography (eluent: ethyl acetate/hexane=1/5) and desired fractions were concentrated under reduced pressure. The residue was purified by column chromatography on octadecylsilica (ODS) (eluent: methanol/water=4/1) and then crystallized from diisopropyl ether to yield propyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 23, 60 mg) as colorless crystals.

Workup

  1. temperatureunder reflux for 50 hours
  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. concentrationdesired fractions were concentrated under reduced pressure
  9. customThe residue was purified by column chromatography on octadecylsilica (ODS) (eluent: methanol/water=4/1)
  10. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-43707ced58324a57a840ce8378e753a2
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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