Potassium Carbonate → 2-(4-Bromo-2-fluorophenyl)-1,2-thiazolidine-1,1-dione

HRID 858642Notes

Reaction equation

HRID 858642 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])=[C:4]([F:16])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[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])=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 43654020N-(4-bromo-2-fluorophenyl)-3-chloropropane-1-sulfonamide

Product 1

HCID 246946312-(4-Bromo-2-fluorophenyl)-1,2-thiazolidine-1,1-dioneYield 122.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-bromo-2-fluorophenyl)-3-chloropropane-1-sulfonamide (8.27 g, 0.025M) and potassium carbonate (5.10 g, 0.0375M) was dissolved in dimethylformamide (50 ml) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred for a further 24 hrs after which time it was partitioned between diethylether (500 ml) and water (500 ml). The organics were washed with 1N HCl (300 ml) and then water (100 ml) The organics were then dried over magnesium sulfate, filtered and the solvent concentrated in vacuuo to afford the title compound as a brown oil (9.0 g). 1H NMR (CDCl3): δ 2.40–2.50 (m, 2H), 3.25–3.40 (m, 2H), 4.00 (m, 2H); 6.78 (m, 2H), 7.10 (d, J=2.56 Hz, 1H),).

Workup

  1. customwas partitioned between diethylether (500 ml) and water (500 ml)
  2. washThe organics were washed with 1N HCl (300 ml)
  3. dry with materialwater (100 ml) The organics were then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuuo

Sources & evidence

ORD record
ord-cacfa1475fde4d61b75b776c2bf59f37
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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