Potassium Carbonate → HCID 89459987, compound

HRID 1776607Notes

Reaction equation

HRID 1776607 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C=O)C.O>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 3288660HCID 3288660, compound

Product 1

HCID 89459987HCID 89459987, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(4-(methylthio)phenyl)methanesulfonamide (200 mg, 0.920 mmol) was dissolved in DMF (3 ml). K2CO3 (254 mg, 1.841 mmol) and tert-butyl 2-bromoacetate (359 mg, 1.841 mmol) were added, and the reaction was stirred at RT for 4 hours. The reaction mixture was diluted with water and filtered. The precipitate was dissolved in EtOAc and extracted with water and HCl 1M, dried over Na2SO4 and concentrated under vacuum to give tert-butyl 2-(N-(4-(methylthio)phenyl)methylsulfonamido)acetate (220 mg, 72.1% yield).

Workup

  1. filtrationfiltered
  2. dissolutionThe precipitate was dissolved in EtOAc
  3. extractionextracted with water and HCl 1M
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1a481a72d13d457a84dd966a01f6f42b
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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