Allyl bromide → 1-allyl-6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline

HRID 2397550Notes

Reaction equation

HRID 2397550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[NH:12][C:13]([CH2:15][CH3:16])=[N:14][C:6]1=[N:5]2.[O-]CC.[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O.O1CCCC1>[CH2:22]([N:12]1[C:7]2=[N:8][C:9]3[C:4]([N:5]=[C:6]2[N:14]=[C:13]1[CH2:15][CH3:16])=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=3)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 1194401-Hydroxyethyl radicalHCID 1784375416-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline

Product 1

HCID 214359881-allyl-6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A mixture of 75 parts of 6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline, 85 parts of thallous ethoxide, and 600 parts of 2:1 anhydrous dimethylformamide-tetrahydrofuran was stirred at room temperature for 1 hour. Allyl bromide (50 parts) was added in one portion, and the mixture was stirred for an additional hour, followed by heating for 30 minutes on a steam bath. The mixture was filtered, and the filtrate was diluted with 2000 parts of water. The filtrate was extracted with three 500 -part portions of chloroform, and the combined extracts dried (potassium carbonate) and evaporated in vacuo. The residue was dissolved in 500 parts of benzene and decolorized (silica gel). The benzene was removed in vacuo and the crude product recrystallized from 95:5 ether-ethanol to yield 24 parts of 1-allyl-6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline, m.p. 117°-121°.

Workup

  1. stirringthe mixture was stirred for an additional hour
  2. temperatureby heating for 30 minutes on a steam bath
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was diluted with 2000 parts of water
  5. extractionThe filtrate was extracted with three 500 -part portions of chloroform
  6. dry with materialthe combined extracts dried (potassium carbonate)
  7. customevaporated in vacuo
  8. dissolutionThe residue was dissolved in 500 parts of benzene
  9. customThe benzene was removed in vacuo
  10. customthe crude product recrystallized from 95:5 ether-ethanol

Sources & evidence

ORD record
ord-46f970a8f0524d309c0f9f79e27bbdfb
Source dataset
uspto-grants-1977_05
Patent number
US04022777

Reaction notes

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