Ethyl Acetate → HCID 22119981, compound

HRID 1274578Notes

Reaction equation

HRID 1274578 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][S:22][CH3:23])[C:17]=3[CH:24]=2)[C:3]1=[O:25].ClC1C=C(C=CC=1)C(OO)=[O:31].C(OCC)(=O)C>C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][S:22]([CH3:23])=[O:31])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 22119947HCID 22119947, compound

Product 1

HCID 22119981HCID 22119981, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-methyl-3-{3-[(methylthio)methyl]-1,2-benzisothiazol-5-yl}-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.740 g, 1.90 mmol) in methylene chloride is treated with 3-chloroperoxybenzoic acid (0.580 g, 60%, 2.00 mmol), stirred at room temperature for five minutes, diluted with additional methylene chloride, washed with 5% sodium carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Flash column chromatography of the solid using silica gel and a 10% ethyl acetate in methylene chloride solution gives the title product as a white solid which is identified by NMR spectral analysis.

Workup

  1. washwashed with 5% sodium carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a solid

Sources & evidence

ORD record
ord-5da1771473924770a7e5532ff9e3de34
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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