m-Chloroperbenzoic acid → 4-{5-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[1,2,4]triazol-3-yl}-pyridine 1-oxide

HRID 273169Notes

Reaction equation

HRID 273169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]3[N:16]([CH3:26])[C:17]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[N:18][N:19]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][S:14][C:15]3[N:16]([CH3:26])[C:17]([C:20]4[CH:25]=[CH:24][N+:23]([O-:35])=[CH:22][CH:21]=4)=[N:18][N:19]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67070566HCID 67070566, compound

Product 1

HCID 670709184-{5-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[1,2,4]triazol-3-yl}-pyridine 1-oxideYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{5-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-4-methyl-4H-[1,2,4]triazol-3-yl}-pyridine and wet 57%-86% MCPBA (52.4 mg, 0.20-0.30 mmol) were dissolved in dichloromethane (4 ml) and stirred for 16 h. The reaction mixture was purified via reversed phase preparative LC to give the title compound (7.5 mg, 8%). 1H NMR (CDCl3), δ (ppm): 8.33 (d, 2 H), 8.06 (m, 1 H), 7.96 (m, 1 H), 7.67 (d, 2 H), 7.57 (m, 1 H), 7.46 (apparent t, 1 H), 4.60 (s, 2 H), 3.71 (s, 3 H).

Workup

  1. customThe reaction mixture was purified via reversed phase preparative LC

Sources & evidence

ORD record
ord-394d33a0142845faaea9745c69a9653f
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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