Sodium Thiosulfate → HCID 178504726, compound

HRID 1881959Notes

Reaction equation

HRID 1881959 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:19][C:20]([C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])=[CH:21][N:22]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCCl>[Cl:28][C:21]1[N:22]=[C:18]([CH:7]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[NH:19][C:20]=1[C:23]([CH:25]1[CH2:27][CH2:26]1)=[O:24]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 59331391HCID 59331391, compound

Product 1

HCID 178504726HCID 178504726, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (12 mL) of (2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)(cyclopropyl)methanone in 1,2-dichloroethane was added N-chlorosuccinimide (0.091 g) and the mixture was stirred at 100° C. for 6 hr. To the reaction mixture were successively added saturated aqueous sodium hydrogen carbonate solution and 1 mol/L aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was successively purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio) and thin layer chromatography (ethyl acetate:hexane=50:50), and recrystallized from diisopropyl ether-hexane to give the title compound (0.016 g, yield 9%) as colorless crystals. melting point 95-97° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was successively purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50, volume ratio) and thin layer chromatography (ethyl acetate:hexane=50:50)
  6. customrecrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-a0ca716bd9b8437f9d61f840fe69b567
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…