Dimethylformamide → HCID 70469256, compound

HRID 64583

Reaction equation

HRID 64583 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:16](C)=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Br[CH:25]([CH3:32])[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29].[CH3:33]N(C)C=O>O>[CH3:33][C:7]1([O:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH:25]([CH3:32])[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29])=[CH:19][CH:18]=2)[N:8]=[C:9]2[C:14]([CH:13]=[CH:12][CH:11]=[CH:10]2)=[N:15][CH2:16]1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 136705382-(4-Hydroxyphenoxy)-3-methylquinoxalineHCID 54128087Methyl 4-bromo-2-pentenoateHCID 178418361HCID 178418361, compound

Product 1

HCID 70469256HCID 70469256, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a nitrogen atmosphere, add a solution of 5.4 g (0.02 mole) 2-(4-hydroxyphenoxy)-3-methylquinoxaline in 30 cc dimethylformamide to 0.9 g (0.02 mole) 57% sodium hydride in 20 cc dimethylformamide at about 20° C. When the evolution of hydrogen ceases, add 3.9 g (0.02 mole) methyl 4-bromo-2-pentenoate. Heat the reaction mixture at approximately 80° C. until the reaction is complete. Pour the reaction mixture into water and extract with ether. Combine the ethereal extracts and dry over magnesium sulfate. Removal of the ether gives the desired product.

Workup

  1. extractionextract with ether
  2. dry with materialdry over magnesium sulfate
  3. customRemoval of the ether

Sources & evidence

ORD record
ord-aa9f6b8071fc48d085f88192195dc687
Source dataset
uspto-grants-1986_09
Patent number
US04609396

Linked notes

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