Dimethyl Sulfoxide → HCID 13749601, compound

HRID 1789367Notes

Reaction equation

HRID 1789367 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][CH2:12][CH2:13][S:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][CH2:12][CH2:13][S:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13749598HCID 13749598, compound

Product 1

HCID 13749601HCID 13749601, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Procedure

A solution of 27.8 g of dimethylsulfoxide in 50 ml of methylene chloride is added to a solution of 22.6 g of oxalyl chloride in 450 ml of methylene chloride at -60° C. during one hour, and a solution of 32.7 g of 2-(2-chloroethylthio)benzylalcohol in 50 ml of methylene chloride is added thereto. The mixture is stirred for 15 minutes, and a solution of 71.8 g of triethylamine in 50 ml of methylene chloride is added to the mixture at -60° C. The mixture is stirred at the same temperature for 5 minutes and further stirred at room temperature for one hour. Water is added to the mixture, and the methylene chloride layer is collected therefrom. The methylene chloride solution is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is distilled under reduced pressure. 29.7 g of 2-(2-chloroethylthio)benzaldehyde are obtained as an oil. Yield: 91.6%.

Workup

  1. stirringThe mixture is stirred at the same temperature for 5 minutes
  2. stirringfurther stirred at room temperature for one hour
  3. customthe methylene chloride layer is collected
  4. washThe methylene chloride solution is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-7f4ccdacd2124c509852605e00d848bd
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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