Water → HCID 57870886, compound

HRID 2191161Notes

Reaction equation

HRID 2191161 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-6b4c70b105844981a419a201fad474f2
Source dataset
uspto-grants-2012_12
Patent number
USRE043858E1

Reaction notes

Loading…