Potassium Carbonate → 4-[2-(Methylthio)ethylamino]phenyl methyl sulfone

HRID 1789653Notes

Reaction equation

HRID 1789653 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:12][S:13][CH2:14][CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:16][CH2:15][CH2:14][S:13][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 87697(2-(Methylthio)ethyl)amine

Product 1

HCID 220361944-[2-(Methylthio)ethylamino]phenyl methyl sulfoneYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To 8.28 g (47.52 mmol) of 4-fluorophenyl methyl sulfone dissloved in 20 mL DMF was added 5.20 g (57.03 mmol) of 2-(methylthio)ethyl amine (1.2 eq.), followed by 13.13 g (95.04 mmol, 2 eq.) potassium carbonate. The mixture was heated to 65° C. and stirred for 12 h. Upon cooling to room temperature, the mixture was partitioned between EtOAc and brine, dried over MgSO4 and concentrated. Column chromatography, eluting with ethyl acetate/hexane, provided 5.53 g of 4-[2-(methylthio)ethylamino]phenyl methyl sulfone, pure by 1H NMR.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe mixture was partitioned between EtOAc and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washColumn chromatography, eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-6e4fe89c52624b9c8f45d6c2f14b4bb6
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

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