Water → Methyl 4-[4-(4-fluorophenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoate

HRID 501251Notes

Reaction equation

HRID 501251 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][S:11](=[O:14])(=[O:13])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.F[C:16]1[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:30])[CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][S:11](=[O:14])(=[O:13])[N:10]([C:16]3[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:30])[CH:17]=3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate2×HCID 68463636887129-62-6

Product 1

HCID 68462085Methyl 4-[4-(4-fluorophenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoateYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.00 g of 4-(4-fluorophenyl)isothiazolidine 1,1-dioxide, 20.59 g of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate (Journal of Medicinal Chemistry (1997), 40(13), 2017) and 81.75 g of Cs2CO3 were stirred in 500 ml of anhydrous DMF at RT for 5 hours. Then a further 2.00 g of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate were added, and the mixture was stirred at RT for 1 hour and left to stand at RT for 15 hours. The reaction mixture was poured into 1800 ml of water and stirred at RT for 1 hour, and the product was filtered off with suction. The product was then dissolved in 1 l of EA, and the solution was mixed with MgSO4 and activated carbon and stirred at RT for 15 minutes. It was then filtered and the solvent was removed in vacuo. 35.00 g of a colorless foam were obtained.

Workup

  1. waitleft
  2. waitto stand at RT for 15 hours
  3. stirringstirred at RT for 1 hour
  4. filtrationthe product was filtered off with suction
  5. dissolutionThe product was then dissolved in 1 l of EA
  6. additionthe solution was mixed with MgSO4 and activated carbon
  7. stirringstirred at RT for 15 minutes
  8. filtrationIt was then filtered
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-828a5a89407b409191281d8af3dbcdd4
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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