m-Chloroperbenzoic acid → 1-Methyl-3-[3-[4-[(methylsulfinyl)methyl]-1,3-dioxolan-2-yl]-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

HRID 49007Notes

Reaction equation

HRID 49007 reaction equation
[CH3:1][N:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:6](=[O:7])[N:5]([C:14]2[CH:15]=[CH:16][C:17]3[S:21][N:20]=[C:19]([CH:22]4[O:26][CH:25]([CH2:27][S:28][CH3:29])[CH2:24][O:23]4)[C:18]=3[CH:30]=2)[C:3]1=[O:4].ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[CH3:1][N:2]1[C:9]([C:10]([F:11])([F:12])[F:13])=[CH:8][C:6](=[O:7])[N:5]([C:14]2[CH:15]=[CH:16][C:17]3[S:21][N:20]=[C:19]([CH:22]4[O:26][CH:25]([CH2:27][S:28]([CH3:29])=[O:39])[CH2:24][O:23]4)[C:18]=3[CH:30]=2)[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 206341881-Methyl-3-[3-[4-[(methylthio)methyl]-1,3-dioxolan-2-yl]-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

Product 1

HCID 206341861-Methyl-3-[3-[4-[(methylsulfinyl)methyl]-1,3-dioxolan-2-yl]-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracilYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methyl-3-[3-[4-[(methylthio)methyl]-1,3-dioxolan-2-yl]-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil (0.970 g, 21.1 mmol), m-chloroperbenzoic acid (72%, 0.500 g, 21.1 mmol) and methylene chloride is stirred one hour at room temperature and concentrated in vacuo. The residue is taken up in ethyl acetate and washed twice with 5% aqueous sodium carbonate and once with brine. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to a white solid, which is chromatographed on silica gel with ethanol-ethyl acetate to afford the title compound as a white solid (0.700 g, 70.0%, mp 72-75° C.) which is identified by IR and NMR spectral analysis.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed twice with 5% aqueous sodium carbonate and once with brine
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo to a white solid, which
  5. customis chromatographed on silica gel with ethanol-ethyl acetate

Sources & evidence

ORD record
ord-0b135d08b5714e00b017489d0509413a
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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