Dimethyl Sulfoxide → HCID 23131805, compound

HRID 1669351Notes

Reaction equation

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

Participants

Conditions

Temperature: -60 °C

Procedure

To a mixture of 2.64 g of oxalyl chloride and 50 ml of dichloromethane was added dropwise a solution of 3.24 g of dimethyl sulfoxide in 30 ml of dichloromethane at −60° C. for 10 minutes. After stirred at −60° C. for 20 minutes, a solution of 3.72 g of 3-[(2-methoxyethyl)aminocarbonylamino]benzyl alcohol in 30 ml of dichloromethane was added dropwise at −60° C. for 1 hour. After stirred at −60° C. for 15 minutes, 9.24 g of triethylamine was added dropwise at −60° C. for 25 minutes. After stirred at room temperature for 1 hour, water was added to the reaction solution, and the layers were separated. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain 2.79 g of 3-[(2-methoxyethyl)aminocarbonylamino]benzaldehyde [Compound No. (i)] as a white crystal.

Workup

stirringAfter stirred at −60° C. for 15 minutes
stirringAfter stirred at room temperature for 1 hour
customthe layers were separated
washThe organic layer was washed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-984f7a5f27c340eeba9b21057bf13789
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989478B2

Reaction notes

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