Dimethyl Sulfoxide → HCID 23331769, compound

HRID 224664Notes

Reaction equation

HRID 224664 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:19]1[CH:23]=[C:22]([CH3:24])[N:21]([CH:25]([CH3:28])[CH2:26][OH:27])[C:20]=1[CH3:29])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([C:19]1[CH:23]=[C:22]([CH3:24])[N:21]([CH:25]([CH3:28])[CH:26]=[O:27])[C:20]=1[CH3:29])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 194460[1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

Product 1

HCID 23331769HCID 23331769, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Dimethylsulfoxide (625 mg, 8 mmoles) was dissolved in 20 ml of methylene chloride, and the solution was cooled to -78° C. with a dry ice-acetone bath. Oxalyl chloride (762 mg, 6 mmoles) was added to the solution, and the mixture was stirred at the same temperature for 30 minutes. Then, 1.027 g (4 mmoles) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)-2-methylethanol dissolved in 12 ml of methylene chloride was added dropwise to the mixture. The mixture was stirred for 30 minutes, and then 1.6 ml of triethylamine was added dropwise. The mixture was warmed up gradually to room temperature. The reaction mixture was shaken with 50 ml of methylene chloride and 50 ml of water to separate an organic layer. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to form a dark scarlet oil. The oil was chromatographed on a column containing 50 g of silica gel using benzene/ethyl acetate (20/1) as an eluent. The fractions were collected each in an amount of 50 ml. From the 5th to 14th fractions, 500 mg (50%) of compound (502) was obtained.

Workup

  1. additionwas added dropwise to the mixture
  2. stirringThe mixture was stirred for 30 minutes
  3. temperatureThe mixture was warmed up gradually to room temperature
  4. customto separate an organic layer
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto form a dark scarlet oil
  9. customThe oil was chromatographed on a column
  10. additioncontaining 50 g of silica gel
  11. customThe fractions were collected each in an amount of 50 ml

Sources & evidence

ORD record
ord-479e4286490545faa8c453ab6337c52f
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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