Sodium hydride → HCID 53998497, compound

HRID 1614550Notes

Reaction equation

HRID 1614550 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[C:8](=[O:17])[NH:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[H][H].[CH2:20](Br)[CH:21]=[C:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH2:20]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:16]=[C:7]([CH2:6][CH2:5][CH2:4][OH:3])[C:8]1=[O:17])[CH:21]=[C:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 54036684HCID 54036684, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53998497HCID 53998497, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 9.68 g of 60% sodium hydride in 50 ml of anhydrous DMF, there is slowly added a solution of 44.9 g of 3-(3-hydroxy propyl) 1,2-dihydro 2-oxo quinoxaline (obtained in accordance with 1.1) in 450 ml of DMF. The solution is agitated until completion of the liberation of hydrogen, whereupon 36 g of prenyl bromide are added. The resultant solution is agitated overnight at room temperature and then evaporated to dryness under reduced pressure. The brown residue is treated with 150 ml of water and 400 ml of methylene chloride. After evaporation under vacuum, a beige solid is obtained which is recrystallized from 200 ml of toluene. In this way there are isolated 33.8 g of compound 1 in the form of pale yellow crystals.

Workup

  1. additionare added
  2. customevaporated to dryness under reduced pressure
  3. additionThe brown residue is treated with 150 ml of water and 400 ml of methylene chloride
  4. customAfter evaporation under vacuum
  5. customa beige solid is obtained which
  6. customis recrystallized from 200 ml of toluene

Sources & evidence

ORD record
ord-105604e94a164ad0882bc0d24f5bc49a
Source dataset
uspto-grants-1993_03
Patent number
US05198441

Reaction notes

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