Methyl iodide → HCID 60169254, compound

HRID 1518693Notes

Reaction equation

HRID 1518693 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](=[O:16])[CH2:14][CH3:15])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[C:9]=2[CH3:27])=[CH:4][CH:3]=1.[C:28]([O-])([O-])=O.[K+].[K+].CI>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](=[O:16])[CH2:14][CH3:15])=[C:10]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH:26][CH3:28])(=[O:24])=[O:25])=[CH:19][CH:18]=3)[C:9]=2[CH3:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 601679584-[5-(4-Chlorophenyl)-4-methyl-2-(1-oxopropyl)-3-thienyl]benzenesulfonamide2×

Product 1

HCID 60169254HCID 60169254, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(5-(4-chlorophenyl)-4-methyl-2-propionylthiophen-3-yl)benzenesulfonamide (Compound 1, 0.50 g, 1.19 mmol) in acetonitrile (15 ml) was added K2CO3 (0.25 g, 1.84 mmol) at room temperature and stirred for 15 minutes. To this was added methyl iodide (0.20 g, 0.08 ml, 1.42 mmol). The so obtained mixture was stirred at room temperature for 15 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The concentrated mass was diluted with water (20 ml). The mixture so obtained was extracted with ethyl acetate (3×30 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain a crude product. The crude product so obtained was purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain first title compound (0.05 g, 9.38%) and second title compound (0.045 g, 8.7%).

Workup

  1. customThe so obtained mixture
  2. stirringwas stirred at room temperature for 15 hr
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. additionThe concentrated mass was diluted with water (20 ml)
  5. customThe mixture so obtained
  6. extractionwas extracted with ethyl acetate (3×30 ml)
  7. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a crude product
  10. customThe crude product so obtained
  11. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-3c845dc344944b36a1a5b490004686a9
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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