Water → HCID 11426638, compound

HRID 431908Notes

Reaction equation

HRID 431908 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Br[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.O.C[N:30](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]([Br:1])[CH:10]=2)[O:8][N:30]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 887075-Bromonicotinic acidHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 11426638HCID 11426638, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion, 5-bromonicotinoyl chloride was prepared from 5-bromonicotinic acid (2.02 g, 10 mmol). Treatment of the acid chloride with pyrid-2-ylamidoxime (1.37 g, 10 mmol) and triethylamine (4.04 g, 40 mmol) in dichloromethane (20 mL), followed by heating in dimethylformamide (20 mL) at 120° C. for 16 hours. After this time water was added and the precipitate collected and dried. Filtration through silica gel using dichloromethane followed by trituration with hexane afforded 2.58 g (85%) of 3-(2-pyridyl)-5-(5-bromopyrid-3-yl)-1,2,4-oxadiazole.

Workup

  1. customthe precipitate collected
  2. customdried
  3. filtrationFiltration through silica gel

Sources & evidence

ORD record
ord-b06b9b6e032649e0bf18c4d2c1fd5e80
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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