m-Chloroperbenzoic acid → HCID 18427299, compound
Reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([S:20][CH3:21])=[CH:15][N:14]=1>C(Cl)Cl>[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([S:20]([CH3:21])=[O:9])=[CH:15][N:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
8.9 g (0.052 mol) of m-chloroperbenzoic acid were added, a little at a time, to a suspension of 10 g (0.052 mol) of 2,3-dichloro-5-methylthiopyridine in 60 ml of methylene chloride. After the mixture had been stirred for 2 hours at approximately 20° C., a further 0.9 g (5 mmol) of m-chloroperbenzoic acid was added. The mixture was subsequently refluxed for a further 2 hours. After cooling, the solids were separated off, whereupon the organic phase was washed once with sodium hydrogen sulfite, once with sodium hydrogen carbonate and once with water. After the mixture had been dried over sodium sulfate, it was concentrated. The crude product which was obtained as a red oil was purified by means of flash chromatography over silica gel (eluent: cyclohexane/ethyl acetate=1:1). Yield: 6.3 g (58%) as a brown oil; 1H-NMR (in d6 dimethyl sulfoxide): δ [ppm]=2.9 (s, CH3); 8.4 and 8.7 (2×d, pyr H).
Workup
- temperatureThe mixture was subsequently refluxed for a further 2 hours
- temperatureAfter cooling
- customthe solids were separated off, whereupon the organic phase
- washwas washed once with sodium hydrogen sulfite, once with sodium hydrogen carbonate and once with water
- dry with materialAfter the mixture had been dried over sodium sulfate, it
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-91d0930d33244732a9fde7ce4f754f71
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448205B1
Reaction notes
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