Water → HCID 13007359, compound

HRID 895784Notes

Reaction equation

HRID 895784 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH2:22][O:23][CH2:24][CH3:25].O>CN(C)C=O>[N:1]([CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH2:22][O:23][CH2:24][CH3:25])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 13007358HCID 13007358, compound

Product 1

HCID 13007359HCID 13007359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (14.7 g) was added to a solution of 1-(2-chloroethyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4amine (22.8 g prepared according to the method of Part F) in N,N-dimethylformamide (75 mL). The reaction mixture was heated at reflux for several hours and then allowed to cool to ambient temperature overnight. The reaction mixture was poured into water (100 ml) and then extracted 3 times with ethyl acetate. The extracts were combined, washed 3 times with water, dried over magnesium sulfate, filtered and then concentrated to dryness under vacuum to provide crude 1-(2-azidoethyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin4-amine as an oil.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for several hours
  4. extractionextracted 3 times with ethyl acetate
  5. washwashed 3 times with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-870e3d79508c499b9ddc18e1311c636e
Source dataset
uspto-grants-2005_07
Patent number
US06916925B1

Reaction notes

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