Diethyl Ether → HCID 22119877, compound

HRID 1274552Notes

Reaction equation

HRID 1274552 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[CH2:25]([O:27]CC)C>ClCCCl.CO.C(Cl)Cl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:25][O:27][CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1

Participants

7

Reactant 2

HCID 3283Diethyl EtherHCID 22119928HCID 22119928, compound

Product 1

HCID 22119877HCID 22119877, compound

Reagents, catalysts & solvents 4

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.750 g, 1.79 mmol) in 1,2-dichloroethane is diluted with methanol, treated with silver trifluoromethanesulfonate (0.610 g, 2.37 mmol), stirred overnight at room temperature, and filtered through diatomaceous earth. The resultant filtrate is washed with saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel, and 2% and 5% diethyl ether in methylene chloride solutions gives the title product as a white solid (0.600 g, mp 161-163° C.) which is identified by 1H NMR spectral analysis.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. washThe resultant filtrate is washed with saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a solid

Sources & evidence

ORD record
ord-81181f456c2940489adb8e73cdf9a940
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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