N-bromobutanimide → 3-(2-Pyridyl)-5-(3-bromomethyl-5-cyanophenyl)-1,2,4-oxadiazole

HRID 431949Notes

Reaction equation

HRID 431949 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)[O:9][N:8]=1.[Br:21]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.ClCCl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:13]=[C:14]([C:19]#[N:20])[CH:15]=[C:16]([CH2:18][Br:21])[CH:17]=2)[O:9][N:8]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 9856535HCID 9856535, compound

Product 1

HCID 219425773-(2-Pyridyl)-5-(3-bromomethyl-5-cyanophenyl)-1,2,4-oxadiazoleYield 91.3%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(2-pyridyl)-5-(3-cyano-5-methylphenyl)-1,2,4-oxadiazole (0.5 g, 1.91 mmol), N-bromosuccinimide (0.339 g, 1.91 mmol), and benzoyl peroxide (0.0010 g, 0.04 mmol) in carbon tetrachloride (25 mL) was heated at 80° C. for 18 hours. After this time the reaction mixture was cooled and diluted with dichloromethane. The organic solution was washed with water and brine to afford 0.595 g (91%) of 3-(2-pyridyl)-5-(3-bromomethyl-5-cyanophenyl)-1,2,4-oxadiazole.

Workup

  1. temperatureAfter this time the reaction mixture was cooled
  2. washThe organic solution was washed with water and brine

Sources & evidence

ORD record
ord-f14f5b914977484fa940341a7c3db352
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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