Dimethylformamide → 3-(Pyridin-2-yl)-5-(5-chloro-pyrid-3-yl)-1,2,4-oxadiazole

HRID 431909Notes

Reaction equation

HRID 431909 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH:20]=1)C(O)=O.C([N:23]([CH2:26]C)CC)C.C[N:29](C)C=O>ClCCl>[N:14]1[CH:13]=[CH:12][CH:20]=[CH:16][C:15]=1[C:26]1[N:23]=[C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[O:8][N:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2479865-Chloronicotinic acidHCID 219426495-Chloronicotinoyl chloride

Product 1

HCID 98564743-(Pyridin-2-yl)-5-(5-chloro-pyrid-3-yl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion, 5-chloronicotinoyl chloride was prepared from 5-chloronicotinic acid (157 mg, 1 mmol). Treatment of the acid chloride with pyrid-2-ylamidoxime (137 mg, 1 mmol) and triethylamine (404 mg, 4 mmol) in dichloromethane (2 mL), followed by heating in dimethylformamide (2 mL) at 120° C. for 3 hours afforded 149 mg (58%) of 3-(2-pyridyl)-5-(5-chloro-pyrid-3-yl)-1,2,4-oxadiazole (149 mg, 57.6%).

Sources & evidence

ORD record
ord-1d82863d148c459884d8b013a31796a2
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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