Dimethyl Sulfoxide → HCID 68930950, compound

HRID 2362497Notes

Reaction equation

HRID 2362497 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:15]1[N:16]([CH2:28][CH2:29][CH2:30][CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[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][C:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[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 69507123HCID 69507123, compound

Product 1

HCID 68930950HCID 68930950, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of DMSO (1.35 g, 17.3 mmol) in dichloromethane (22 mL) was cooled in a dry ice/acetone bath and stirred. Oxalyl chloride (1.61 g, 12.7 mmol) was added dropwise, followed by a solution of 4-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-ol (4.3 g, 11.5 mmol) in dichloromethane (55 mL). After five minutes, triethylamine (3.49 g, 34.5 mmol) was added, and the mixture was allowed to warm to room temperature. After the addition of chloroform (300 mL), the mixture was washed successively with a saturated ammonium chloride solution (100 mL) and a saturated aqueous sodium bicarbonate solution (100 mL), dried over sodium sulfate, filtered, and concentrated to provide 4-(2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-phenylbutan-1-one (4.15 g) as an off-white solid.

Workup

  1. washthe mixture was washed successively with a saturated ammonium chloride solution (100 mL)
  2. dry with materiala saturated aqueous sodium bicarbonate solution (100 mL), dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-05e57082d82d4475b9cbf308692bd7d7
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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