Acetone → HCID 21703069, compound

HRID 2053062Notes

Reaction equation

HRID 2053062 reaction equation
C(C1C=CSC=1[S:10]([NH2:13])(=[O:12])=[O:11])(C)(C)C.[C:14](=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22].[CH3:23][C:24]([CH3:26])=O>>[CH2:21]([NH:13][S:10]([C:24]([CH3:26])([CH3:14])[CH3:23])(=[O:11])=[O:12])[CH3:22]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 20131667HCID 20131667, compound

Product 1

HCID 21703069HCID 21703069, compoundYield 85%

Procedure

tert-Butyl-thiophene sulfonamide available from Preparative Example 16.1 Step A (164 mg, 050 mmol) was treated with potassium carbonate (700 mg. 5 mmol) and iodoethane (0.4 mL 5 mmol) in acetone and refluxed for 1.5 d. The mixture was filtered, and the solid material was washed with methylene chloride. The combined filtrated and washing were concentrated purified by flash column chromatography eluting with 0 to 30% methylene chloride in hexanes. Removal of solvents afforded the ethyl-tert-butyl-sulfonamide (151 mg, 85%).

Workup

  1. temperaturerefluxed for 1.5 d
  2. filtrationThe mixture was filtered
  3. washthe solid material was washed with methylene chloride
  4. filtrationThe combined filtrated
  5. washwashing
  6. concentrationwere concentrated
  7. custompurified by flash column chromatography
  8. washeluting with 0 to 30% methylene chloride in hexanes
  9. customRemoval of solvents

Sources & evidence

ORD record
ord-e26a0e13a95c49af9fab4cff0dbbc7ef
Source dataset
uspto-grants-2008_02
Patent number
US07326729B2

Reaction notes

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