Potassium Carbonate → 5-(3-Methoxy-phenyl)-3-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole

HRID 732016Notes

Reaction equation

HRID 732016 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[O:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][N:23]1[C:27]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[N:26][N:25]=[C:24]1[SH:33]>C(#N)C>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][S:33][C:24]3[N:23]([CH3:22])[C:27]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[N:26][N:25]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117155623-(Chloromethyl)-5-(3-methoxyphenyl)-1,2,4-oxadiazoleHCID 178481692HCID 178481692, compound

Product 1

HCID 104526765-(3-Methoxy-phenyl)-3-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazoleYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 3-chloromethyl-5-(3-methoxy-phenyl)-[1,2,4]oxadiazole (50 mg, 0.22 mmol), potassium carbonate (92.4 mg, 0.67 mmol), 4-methyl-5-thiophen-2-yl-4H-[1,2,4]triazole-3-thiol (52.8 mg, 0.27 mmol) in acetonitrile (1 ml) at room temperature. Purification was performed by SPE (flash) chromatography using 30-40% ethyl acetate in hexanes afforded 76 mg (90%) of the title compound as a white solid. 1H NMR (CDCl3), δ (ppm): 7.68 (d, 1H), 7.57 (t, 1H), 7.49 (m, 2H), 7.41 (t, 1H), 7.15 (m, 2H), 4.53 (s, 2H), 3.85 (s, 3H), 3.72 (s, 3H). LC-MS (M+1)+386.3.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-d1c24069ec27432e81c1f0526ec31576
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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