Dimethylformamide → HCID 11380097, compound

HRID 431907Notes

Reaction equation

HRID 431907 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:12])=[C:7]([CH:11]=1)C(Cl)=O)#[N:2].[C:13]([C:15]1C=CC(F)=[C:19]([CH:23]=1)[C:20](O)=O)#[N:14].C([N:27](CC)CC)C.[CH3:32][N:33](C)[CH:34]=[O:35]>ClCCl>[N:14]1[CH:13]=[CH:15][CH:23]=[CH:19][C:20]=1[C:32]1[N:33]=[C:34]([C:7]2[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[F:12])[O:35][N:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27784625-Cyano-2-fluorobenzoic acidHCID 21942520HCID 21942520, compound

Product 1

HCID 11380097HCID 11380097, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion, 5-cyano-2-fluorobenzoyl chloride was prepared from 5-cyano-2-fluorobenzoic acid (185 mg, 1.12 mmol). Treatment of the acid chloride with pyrid-2-ylamidoxime (1.153 g, 1.12 mmol) and triethylamine (340 mg, 3.36 mmol) in dichloromethane (3 mL), followed by heating in dimethylformamide (2 mL) at 120° C. for 16 hours, afforded 17 mg (6%) of 3-(2-pyridyl)-5-(5-cyano-2-fluorophenyl)-1,2,4-oxadiazole.

Sources & evidence

ORD record
ord-a1f16d73cfa14769af01e5076c2b8d47
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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