Dimethyl Sulfoxide → 2-[3-(4-Phenylpiperazin-1-yl)propylthio]benzaldehyde

HRID 1789372Notes

Reaction equation

HRID 1789372 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][S:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[CH2:29][OH:30])[CH2:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[C:11]1([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][S:26][C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[CH:29]=[O:30])[CH2:21][CH2:22]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 137680822-[3-(4-Phenylpiperazin-1-yl)propylthio]benzylalcohol

Product 1

HCID 201881712-[3-(4-Phenylpiperazin-1-yl)propylthio]benzaldehydeYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.1 g of dimethylsulfoxide in 5 ml of methylene chloride is added to a solution of 0.894 g of oxalyl chloride in 20 ml of methylene chloride at -50° C. A solution of 2.19 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzylalcohol in 10 ml of methylene chloride is added to the mixture at -50° C., and the mixture is stirred at the same temperature for 15 minutes. 3.24 g of triethylamine are added to the mixture, and the mixture is stirred at -50° C. for 5 minutes and further stirred at room temperature for one hour. The mixture is poured into water, and the aqueous mixture is extracted with methylene chloride. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=1:6). 1.97 g of 2-[3-(4-phenylpiperazin-1-yl)propylthio]benzaldehyde are obtained as an oil. Yield: 90.5%.

Workup

  1. stirringthe mixture is stirred at -50° C. for 5 minutes
  2. stirringfurther stirred at room temperature for one hour
  3. extractionthe aqueous mixture is extracted with methylene chloride
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is purified by silica gel chromatography (solvent, ethyl acetate:chloroform=1:6)

Sources & evidence

ORD record
ord-e1eec7f7add74932a65c6586620a67b0
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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