Dimethyl Sulfoxide → HCID 23537999, compound

HRID 1792378Notes

Reaction equation

HRID 1792378 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH3:30].C(N(CC)CC)C>ClCCl.O>[CH3:29][O:28][C:24]1[CH:23]=[C:22]2[C:27]([CH:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[O:11])[C:19]([C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)([CH3:30])[CH2:20][S:21]2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22033204HCID 22033204, compound

Product 1

HCID 23537999HCID 23537999, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (238 mg, 1.88 mmol) in dichloromethane (5 ml) was added dimethylsulfoxide (316 mg, 3.75 mmol) in dichloromethane (1 ml) at −70° C., which was then stirred at the same temperature for 10 minutes. Next, to the solution was added 4-(6-hydroxyhexyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (500 mg, 1.25 mmol) in dichloromethane (5 ml) at −70° C., which was then stirred at the same temperature for 30 minutes. Then, to the reaction mixture was added triethylamine (1.0 ml, 7.5 mmol) at the same temperature and stirred for 30 minutes and warmed to room temperature. After the reaction was completed, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was used to next step without purification (470 mg, yield: 94%).

Workup

  1. stirringwhich was then stirred at the same temperature for 30 minutes
  2. stirringstirred for 30 minutes
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was used to next step without purification (470 mg, yield: 94%)

Sources & evidence

ORD record
ord-bb0f4149bade4b4d8ec79d5f0cbb71ff
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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