Cesium carbonate → 2-(4-Bromophenyl)-1lambda~6~,2-thiazolidine-1,1-dione

HRID 1591832Notes

Reaction equation

HRID 1591832 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH2:13][CH2:14]Cl)(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][S:9]2(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 43654432HCID 43654432, compound

Product 1

HCID 125442182-(4-Bromophenyl)-1lambda~6~,2-thiazolidine-1,1-dioneYield 74%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

N-(4-Bromophenyl)-3-chloropropane-1-sulfonamide (1.0 g, 3.2 mmol) was dissolved in DMF, Cs2CO3 (1.56 g, 4.8 mmol) was added, and the mixture was stirred for 3 hours. The mixture was then diluted with ether, washed with water, 2N HCl, brine, dried over MgSO4, and concentrated. The crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-60% ethyl acetate in hexane) to afford 0.65 g (74%) 2-(4-bromophenyl)isothiazolidine 1,1-dioxide.

Workup

  1. washwashed with water, 2N HCl, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified via Isco chromatography (the Redisep® column, silica, gradient 5-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-badd3839ed964d90b8c6c5b71323ed65
Source dataset
uspto-grants-2007_11
Patent number
US07291643B2

Reaction notes

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