Dimethyl Sulfoxide → HCID 57455395, compound

HRID 1623119Notes

Reaction equation

HRID 1623119 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:14]1[N:15]([CH2:27][CH2:28][CH2:29][CH:30]([OH:32])[CH3:31])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1)[CH2:12][CH3:13].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:11]([C:14]1[N:15]([CH2:27][CH2:28][CH2:29][C:30](=[O:32])[CH3:31])[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:26]=1)[CH2:12][CH3:13]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 57455394HCID 57455394, compound

Product 1

HCID 57455395HCID 57455395, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (4.99 mL, 57.28 mmol) was added to a mixture of methyl sulfoxide (DMSO) (5.54 g, 71.46 mmol) in dichloromethane (50 mL) at −78° C. and stirred for 5 minutes. 5-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-ol (14.2 g, 47.74 mmol) was added dropwise, followed by the addition of triethylamine (19.96 mL, 143.2 mmol). The reaction was allowed to warm to ambient temperature and the reaction was stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, filtered over magnesium sulfate, and concentrated under reduced pressure to afford 10.7 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one as a brown oil.

Workup

  1. stirringthe reaction was stirred for 2 hours
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. filtrationfiltered over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7b6662125024c24b216e25290d62559
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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