Cesium carbonate → HCID 68462811, compound

HRID 501247Notes

Reaction equation

HRID 501247 reaction equation
F[C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:16])[CH:3]=1.[C:17]1([CH:23]2[CH2:27][S:26](=[O:29])(=[O:28])[NH:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C>[O:28]=[S:26]1(=[O:29])[CH2:27][CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][N:25]1[C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoateHCID 154151404-phenyl-1lambda6,2-thiazolidine-1,1-dione

Product 1

HCID 68462811HCID 68462811, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

600 mg of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate (Journal of Medicinal Chemistry (1997), 40(13), 2017), 600 mg of 4-phenyl-isothiazolidine 1,1-dioxide (Pharmaceutical Chemistry Journal (Translation of Khimiko-Farmatsevticheskii Zhurnal) (2000), Volume Date 1999, 33(11), 598) and 2.379 g of Cs2CO3 were stirred in 20 ml of anhydrous DMF at RT for 4 hours. The reaction mixture was then poured into 220 ml of a half-saturated aqueous NaHCO3 solution and extracted 3 times with 140 ml of EA each time. After drying over Na2SO4, the solvent was removed in vacuo. Chromatography on silica gel with DIP afforded 865 mg of a colorless oil.

Workup

  1. extractionextracted 3 times with 140 ml of EA each time
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2cf96c77b421447fa4db11b2263131e2
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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