Sodium hydride → Imidazo[1,2-a]quinoxalin-4(5H)-one

HRID 389077Notes

Reaction equation

HRID 389077 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)=[O:10].[H-].[Na+].CO.C(Cl)Cl>CN(C)C(=O)C>[CH:13]1[N:12]2[C:4]3[C:3]([NH:8][C:9](=[O:10])[C:11]2=[N:15][CH:14]=1)=[CH:2][CH:7]=[CH:6][CH:5]=3

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 42258992'-Fluoro-2-imidazolecarboxanilideHCID 21226129Dichloromethane methanol

Product 1

HCID 15667665Imidazo[1,2-a]quinoxalin-4(5H)-oneYield 79%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

10 (2 g, 9.75 mmol) is solubilized in N,N-dimethylacetamide (DMA) (80 ml) before adding sodium hydride (NaH 60% by weight) (1.5 g, 62 mmol). The mixture thus obtained is carried at reflux for 15 h. The reaction is monitored by TLC, eluent: MeOH/CH2Cl2 (10/90). This not being complete, 2 equivalents of NaH are added. The mixture is left at reflux for 30 h. Once the reaction is complete, the mixture is concentrated under vacuum, then to the dry residue are added water and a saturated ammonium chloride aqueous solution. A brown precipitate is formed, which is collected by filtration, washed with water and dried under vacuum. A beige solid (1.42 g, 79%) is obtained. Analysis calculated for C10H7N3O: C, 64.86; H, 3.81; N, 22.69. Experimental: C, 64.44; H, 4.03; N, 22.98.

Workup

  1. customThe mixture thus obtained
  2. temperatureat reflux for 15 h
  3. waitThe mixture is left
  4. temperatureat reflux for 30 h
  5. concentrationthe mixture is concentrated under vacuum
  6. additionto the dry residue are added water
  7. customA brown precipitate is formed
  8. filtrationwhich is collected by filtration
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-b6a91bab3e05408c912a996e177d57a2
Source dataset
uspto-grants-2013_02
Patent number
US08378098B2

Reaction notes

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