Methyl iodide → HCID 66620306, compound

HRID 415556Notes

Reaction equation

HRID 415556 reaction equation
I[CH3:2].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:15](=[S:28])[NH:14][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1.[OH-].[NH4+]>O.C(O)C.C(Cl)(Cl)Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[N:16]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[C:15]([S:28][CH3:2])=[N:14][C:9]=3[CH:10]=[N:11][C:12]=2[CH:13]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14923Ammonium HydroxideHCID 86633746HCID 86633746, compound

Product 1

HCID 66620306HCID 66620306, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

Iodomethane (0.89 mL, 14 mmol) was added to a suspension of tert-butyl 3-(7-bromo-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate (4 g, 9 mmol) in deionized water (25 mL), ethanol (25 mL), and ammonium hydroxide (5 mL), and the reaction was stirred for two hours at room temperature and then diluted with chloroform and water. The aqueous layer was separated and extracted four times with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was dried under high vacuum to provide 2.7 g of tert-butyl 3-(7-bromo-2-(methylthio)-1H-imidazo[4,5-c]quinolin-1-yl)propylcarbamate.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted four times with chloroform
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe crude product was dried under high vacuum

Sources & evidence

ORD record
ord-9c779d446aa145a19caeaa27a7fbb1f4
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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