Diethyl Ether → HCID 18706554, compound

HRID 1422261Notes

Reaction equation

HRID 1422261 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([CH2:16][CH2:17][CH2:18]O)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C([Br:35])C=C.C(OCC)C>C(#N)C>[Br:35][CH2:18][CH2:17][CH2:16][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7841Allyl bromideHCID 682631,1'-CarbonyldiimidazoleHCID 18706508HCID 18706508, compound

Product 1

HCID 18706554HCID 18706554, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.5 g (1.77 mmol) of 3-(7-chloro-2,3-dimethoxy-quinoxalin-5-yl)-propan-1-ol and 0.287 g (1.77 mmol) of 1,1'-carbonyidiimidazole are placed in 5 ml of acetonitrile under N2. 0.75 ml of allyl bromide is added, and the mixture is then stirred at room temperature for 30 minutes and at reflux for 2 hours. The reaction mixture is cooled to room temperature, diethyl ether is added and extraction is carried out with water, 0.1N hydrochloric acid, saturated sodium hydrogen carbonate solution and brine. The aqueous phases are then washed with diethyl ether. The organic phases are combined, dried over sodium sulfate, filtered over a layer of silica gel and concentrated. 0.438 g (79.9%) of 5-(3-bromopropyl)-7-chloro-2,3-dimethoxy-quinoxaline is obtained in the form of a yellow oil which is used further without further purification.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextraction
  4. washThe aqueous phases are then washed with diethyl ether
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered over a layer of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-03ed82e7ab8a4aef8429ef3b4fe55e33
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

Loading…