m-Chloroperbenzoic acid → HCID 19806755, compound

HRID 1681467Notes

Reaction equation

HRID 1681467 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([O:14][C:15]1[C:19]([Cl:20])=[C:18]([O:21][CH3:22])[S:17][N:16]=1)[CH3:13]>C(Cl)Cl>[CH2:12]([O:14][C:15]1[C:19]([Cl:20])=[C:18]([O:21][CH3:22])[S:17](=[O:6])[N:16]=1)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19806771HCID 19806771, compound

Product 1

HCID 19806755HCID 19806755, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperoxybenzoic acid (100 mg, 0.49 mmol) in methylene chloride (1.5 ml) wad added dropwise with stirring to an ice-cooled solution of 3-ethoxy-4-chloro-5-methoxyisothiazole (87 mg, 0.45 mmol) in methylene chloride (1.0 ml). The solution was then stirred for 12 hours at room temperature. The m-chlorobenzoic acid, which precipitated out of solution, was filtered off. The filtrate was concentrated in vacuo, and the residue was chromatographed on a silica gel column, eluting with toluene followed by chloroform, to give 40 mg of the title compound.

Workup

  1. customThe m-chlorobenzoic acid, which precipitated out of solution
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was chromatographed on a silica gel column
  5. washeluting with toluene

Sources & evidence

ORD record
ord-e7d52bba44f746fc9f186a93bd174063
Source dataset
uspto-grants-1992_12
Patent number
US05171860

Reaction notes

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