Dimethyl Sulfoxide → HCID 11572296, compound

HRID 1669360Notes

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

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 was 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

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

Sources & evidence

ORD record: ord-b79df74bfd934863b7b5993f9bab24d5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989478B2

Reaction notes

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