Water → HCID 57870886, compound

HRID 546349Notes

Reaction equation

HRID 546349 reaction equation
[N:1]1([NH:6][S:7]([CH:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH2:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:21]N1C(=O)CCC1=O.O>O1CCCC1>[Cl:21][C:5]1[N:1]([NH:6][S:7]([CH:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH2:13][CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 57871042HCID 57871042, compound

Product 1

HCID 57870886HCID 57870886, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 mg (0.503 mmol) of ethyl 6-[N-(1H-pyrrol-1-yl)sulfamoyl]-1-cyclohexene-1-carboxylate obtained in Example 31 was dissolved in 3 ml of tetrahydrofuran, and 70 mg (0.528 mmol) of N-chlorosuccinimide was added thereto with stirring under ice-cooling, followed by stirring overnight at room temperature. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel thin layer chromatography (solvent; hexane:ethyl acetate=2:1) and the resulting solid was further washed with isopropyl ether to give 50 mg of the title compound as a white powder (yield: 30%).

Workup

  1. temperaturecooling
  2. stirringby stirring overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. washthe resulting solid was further washed with isopropyl ether

Sources & evidence

ORD record
ord-c07b18e1d18947edb1bcae910a251d88
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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