Methanol → HCID 22119898, compound

HRID 1274633Notes

Reaction equation

HRID 1274633 reaction equation
Br[CH:2]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)[CH3:3].[CH3:26][OH:27]>FC(F)(F)S([O-])(=O)=O.[Ag+].ClCCCl>[CH3:26][O:27][CH:2]([C:4]1[C:8]2[CH:9]=[C:10]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[CH:11]=[CH:12][C:7]=2[S:6][N:5]=1)[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 22119845HCID 22119845, compound

Product 1

HCID 22119898HCID 22119898, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 3-[3-(1-bromoethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.720 g, 0.00166 mol), methanol and 1,2-dichloroethane is added silver trifluoromethane sulfonate (0.510 g, 0.00199 mol). The resultant mixture is stirred 23 hours at room temperature and filtered through diatomaceous earth with ethyl acetate. Saturated sodium bicarbonate is added to the filtrate and the resultant mixture is stirred vigorously for one hour. The organic layer is saved while the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over magnesium sulfate, filtered and concentrated in vacuo to a syrup, which is chromatographed on silica gel with hexanes:ethyl acetate to give the title compound as a white solid (0.660 g, 100%, mp 133-135° C.) which is identified by NMR spectral analysis.

Workup

  1. filtrationfiltered through diatomaceous earth with ethyl acetate
  2. additionSaturated sodium bicarbonate is added to the filtrate
  3. extractionis extracted with ethyl acetate
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a syrup, which
  7. customis chromatographed on silica gel with hexanes

Sources & evidence

ORD record
ord-ab209b2aeecd4245bdec73055e03d776
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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