Methyl iodide → HCID 66619915, compound

HRID 415534Notes

Reaction equation

HRID 415534 reaction equation
[CH3:1][C:2]([CH3:27])([CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[NH:15][C:14]1=[S:26])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].O.[CH2:29](O)C.[OH-].[NH4+].IC>O>[CH3:1][C:2]([CH3:27])([CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[C:14]1[S:26][CH3:29])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14923Ammonium HydroxideHCID 19096565Water ethanolHCID 86633742HCID 86633742, compound

Product 1

HCID 66619915HCID 66619915, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of tert-butyl 2,2-dimethyl-3-(2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (7.78 g, 20.1 mmol) and 100 mL of 1:1 water/ethanol was treated with 20 mL of concentrated ammonium hydroxide and iodomethane (1.50 mL, 24.2 mmol). Two hours later an additional 50 mL of H2O was added, and the precipitate was filtered and rinsed with ether. When the ether was added, the funnel became clogged, so the precipitate was transferred into a flask with the aid of methanol and CH2Cl2. The solvents were removed under reduced pressure to give a light yellow solid. The filtrate was then concentrated under reduced pressure to ˜150 mL of mostly water. Organic material was extracted from this solution using CH2Cl2 (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, combined with the precipitated material, and concentrated under reduced pressure to give tert-butyl 2,2-dimethyl-3-[2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (7.81 g) as a light yellow solid.

Workup

  1. filtrationthe precipitate was filtered
  2. washrinsed with ether
  3. additionWhen the ether was added
  4. customwas transferred into a flask with the aid of methanol and CH2Cl2
  5. customThe solvents were removed under reduced pressure
  6. customto give a light yellow solid
  7. concentrationThe filtrate was then concentrated under reduced pressure to ˜150 mL of mostly water
  8. extractionOrganic material was extracted from this solution
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ba63ded9c6740689c0ed12f6f9a2ae9
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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