Sodium Azide → HCID 23369805, compound

HRID 1900853Notes

Reaction equation

HRID 1900853 reaction equation
I[CH2:2][C:3]1([CH3:22])[O:20][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:21])[NH:11][C:10](=[O:16])[C:9]([CH:17]([CH3:19])[CH3:18])=[CH:8]3.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH2:2][C:3]1([CH3:22])[O:20][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:21])[NH:11][C:10](=[O:16])[C:9]([CH:17]([CH3:19])[CH3:18])=[CH:8]3)=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369844HCID 23369844, compound

Product 1

HCID 23369805HCID 23369805, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Iodomethyl-8-isopropyl-2,3,5-trimethyl-6,7-dihydrofuro[2,3-f]quinoline-7-one (2.10 g, 5.11 mmol) was dissolved in dimethylformamide (75 ml). To the solution, sodium azide (4.50 g, 69.2 mmol) was added, and the mixture was stirred at 150° C. for 4 hours. The reaction mixture was condensed under reduced pressure, and the residue was extracted from chloroform-water. The organic phase was washed with saturated aqueous sodium chloride solution, dried, and condensed under reduced pressure. The residue was separated and purified by silica gel column chromatography (chloroform) to obtain pale yellow crude crystals. The obtained crude was recrystallized from chloroform-ether-hexane to obtain 1.25 g of the title compound (syn:anti=1) as a colorless powder (75.0%).

Workup

  1. customcondensed under reduced pressure
  2. extractionthe residue was extracted from chloroform-water
  3. washThe organic phase was washed with saturated aqueous sodium chloride solution
  4. customdried
  5. customcondensed under reduced pressure
  6. customThe residue was separated
  7. custompurified by silica gel column chromatography (chloroform)
  8. customto obtain pale yellow crude crystals
  9. customThe obtained crude
  10. customwas recrystallized from chloroform-ether-hexane

Sources & evidence

ORD record
ord-23c6193213b74196ac30bc1a02c1ddbc
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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