Dimethyl Sulfoxide → HCID 57464094, compound

HRID 2362495Notes

Reaction equation

HRID 2362495 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:15]1[N:16]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:27]=1)[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl>[CH2:11]([C:15]1[N:16]([CH2:28][CH2:29][CH2:30][CH:31]=[O:32])[C:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[CH:19][C:18]=2[N:27]=1)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57455399HCID 57455399, compound

Product 1

HCID 57464094HCID 57464094, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethyl sulfoxide (DMSO, 7.88 g, 101 mmol) in dichloromethane (130 mL) was cooled in a dry ice/acetone bath and stirred. Oxalyl chloride (9.40 g, 74 mmol) was added dropwise, followed by a solution of 4-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (20.0 g, 67.3 mmol) in dichloromethane (320 mL). After five minutes triethylamine (20.42 g, 202 mmol) was added, and the mixture was allowed to warn to room temperature. After the addition of chloroform (500 mL), the mixture was washed successively with a saturated ammonium chloride solution (200 mL) and a saturated aqueous sodium bicarbonate solution (200 mL), dried over sodium sulfate, filtered, and concentrated to a dark solid. This solid was slurried in diethyl ether until a fine solid resulted. The product was filtered and dried to provide 4-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde (17.9 g) as a light brown solid.

Workup

  1. customto warn to room temperature
  2. washthe mixture was washed successively with a saturated ammonium chloride solution (200 mL)
  3. dry with materiala saturated aqueous sodium bicarbonate solution (200 mL), dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a dark solid
  6. customresulted
  7. filtrationThe product was filtered
  8. customdried

Sources & evidence

ORD record
ord-b4e639b9ef6d4b69af6108bfe51a7470
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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