HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2216842
Notes
Print preview

Reaction equation

HRID 2216842 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 TetrachlorideSolvent
HCID 6344
Dichloromethane
Solvent

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-6ab3fbd6cc114b20afd72dabebff0dbe
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07112595B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes