Sodium Hydroxide → HCID 23684386, compound

HRID 2299211Notes

Reaction equation

HRID 2299211 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]CC)=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].[OH-].[Na+:25]>C(#N)C>[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])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:11])=[O:12].[Na+:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9928140ethyl 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate2×

Product 1

HCID 23684386HCID 23684386, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A solution of ethyl 6-[N-(2, 4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate obtained in Example 3 (Compound 3, 2.5 g) in acetonitrile (288 ml) was admixed with a 1N aqueous solution of sodium hydroxide (228 ml) and the mixture was stirred at 55° C. for 12 hours. The mixture was concentrated under reduced pressure and the residue was purified by CHP-20P column chromatography (eluent: water→methanol/water=1/1). The eluent was concentrated under reduced pressure and the residue was dissolved in water (10 ml) and lyophilized to yield sodium 6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (0.50 g) as white crystals.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by CHP-20P column chromatography (eluent: water→methanol/water=1/1)
  3. concentrationThe eluent was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in water (10 ml)

Sources & evidence

ORD record
ord-96b5195522074415817d7426afe21bfa
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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