m-Chloroperbenzoic acid → HCID 18427288, compound

HRID 1279194Notes

Reaction equation

HRID 1279194 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9][CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([S:9]([CH:10]([CH3:12])[CH3:11])=[O:21])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18427290HCID 18427290, compound

Product 1

HCID 18427288HCID 18427288, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (0.045 mol) of 2,3-dichloro-5-isopropylthiopyridine (as crude product) were reacted with 7.8 g (0.045 mol) of m-chloroperbenzoic acid in 60 ml of methylene chloride by a method similar to Example 1, Precursor β. After the crude product had been purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1), 1.7 g of product of value were obtained. Yield: 16%; m.p.: 62-64° C.; 1H-NMR (in d6 dimethyl sulfoxide): δ [ppm]=1.0 and 1.25 (2×d, 2×CH3); 3.2 (m, CH); 8.3 and 8.5 (2×d, pyr H).

Workup

  1. customAfter the crude product had been purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1), 1.7 g of product of value
  2. customwere obtained

Sources & evidence

ORD record
ord-513d6a4918ba47308bda4009ec9111b6
Source dataset
uspto-grants-2002_09
Patent number
US06448205B1

Reaction notes

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