Sodium Azide → HCID 23369820, compound

HRID 1900840Notes

Reaction equation

HRID 1900840 reaction equation
Br[CH2:2][CH:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:20])[NH:11][C:10](=[O:16])[C:9]([CH3:18])([CH3:17])[CH2:8]3.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.O>[N:21]([CH2:2][CH:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:20])[NH:11][C:10](=[O:16])[C:9]([CH3:18])([CH3:17])[CH2:8]3)=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 23369656HCID 23369656, compound

Product 1

HCID 23369820HCID 23369820, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromomethyl-3,5,8,8-tetramethyl-2,3,6,7,8,9-hexahydrofuro[2,3-f]quinoline-7-one (1.8 g, 5.3 mmol) and 90% sodium azide (3.1 g, 42 mmol) in dimethylformamide (30 ml) was stirred at 150° C. for 2 hours. The reaction mixture was poured in water, followed by extracting with ethyl acetate. The extract was washed with water, and dried. The solvent was evaporated, and the residue was recrystallized from ethyl acetate-hexane. 1.2 g of the title compound was obtained as colorless needles (75.5%).

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a029b44f5b564cddbf00e1270c21e011
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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