Methanol → HCID 21075806, compound

HRID 1373908Notes

Reaction equation

HRID 1373908 reaction equation
[CH:1]1([NH:7][N:8]2[C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]=[CH:12][C:11]=3[N:10]=[C:9]2[CH2:21][O:22][CH2:23][CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1.C(Cl)(Cl)Cl.CO>ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>[CH:1]1([NH:7][N:8]2[C:20]3[C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N+:13]([O-:33])=[CH:12][C:11]=3[N:10]=[C:9]2[CH2:21][O:22][CH2:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 21075805HCID 21075805, compound

Product 1

HCID 21075806HCID 21075806, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

N-Cyclohexyl-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-amine (0.51 g, 1.57 mmol) was placed in a 200 mL round bottom flask, purged with N2 and dissolved in dichloromethane (25 mL). MCPBA (0.484 g, 1.96 mmol, 77% max) was added over a S min period. The reaction was stirred at room temperature under N2. After 2 h, analysis by thin layer chromatography (TLC) (SiO2, 95:5 chloroform:methanol) showed complete conversion. The solution was diluted with dichloromethane (15 mL) and 2% sodium carbonate solution (15 mL). The mixture was transferred to a separatory funnel, and the phases were separated. The organic portion was washed sequentially with 2% sodium carbonate solution (15 mL), water (15 mL) and brine (15 mL), dried (Na2SO4), filtered and then concentrated to yield 0.431 g of N-cyclohexyl-2-(ethoxymethyl)-5-oxido-1H-imidazo[4,5-c]quinolin-1-amine as a tan foam.

Workup

  1. custompurged with N2
  2. dissolutiondissolved in dichloromethane (25 mL)
  3. customThe mixture was transferred to a separatory funnel
  4. customthe phases were separated
  5. washThe organic portion was washed sequentially with 2% sodium carbonate solution (15 mL), water (15 mL) and brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-61bfcda3d92a41dbbd4c97f5d081ca54
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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