Dimethyl Sulfoxide → HCID 11572296, compound

HRID 639730Notes

Reaction equation

HRID 639730 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][OH:23])(=[O:18])=[O:17].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23])(=[O:18])=[O:17]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 65751811HCID 65751811, compound

Product 1

HCID 11572296HCID 11572296, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a mixture of 1.71 g of oxalyl chloride and 30 ml of dichloromethane was added dropwise a solution of 2.3 g of dimethyl sulfoxide in 4 ml of dichloromethane at −60° C. for 35 minutes. After stirred at −60° C. for 20 minutes, a solution of 3.0 g of 3-[(2-methoxyethyl)aminosulfonyl]benzyl alcohol in 22 ml of dichloromethane was added dropwise at −60° C. for 1.5 hours. After stirred at −60° C. for 1 hour, 5.1 ml of triethylamine was added dropwise at −60° C. for 25 minutes. After stirred at room temperature for 3 hours, water was added to the reaction solution, and the layers were separated. The organic layer washed with water, dried over anhydrous sodium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to obtain 2.07 g of oily 3-[(2-methoxyethyl)aminosulfonyl]benzaldehyde [Compound No. (r)].

Workup

  1. stirringAfter stirred at −60° C. for 1 hour
  2. stirringAfter stirred at room temperature for 3 hours
  3. customthe layers were separated
  4. washThe organic layer washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-04ee65390b12401885b0cea9aae0dcbd
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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