Dimethyl Sulfoxide → 4-(Pyridin-2-ylaminomethyl)-benzaldehyde

HRID 7186

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (0.9 ml, 10.32 mmol) in CH2Cl2 (15 ml) at −78° C. was added a solution of DMSO (1.5 ml, 21.11 mmol) in CH2Cl2 (10 ml) and the mixture allowed to stir for 20 min. at −78° C., after which [4-(Pyridin-2-ylaminomethyl)-phenyl]-methanol (1.1 g, 5.13 mmol) in CH2Cl2 (10 ml) was added dropwise. Stirring was continued for 2 hours and then Et3N (2.9 ml, 21.30 mmol) was added dropwise. The cooling bath was removed, stirring was continued for 3 h, and the mixture was diluted with 300 mL ethyl acetate, washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, using 30% ethyl acetate in CH2Cl2, gave the title compound (335 mg, 31%) as a pure white solid.

Workup

stirringStirring
waitwas continued for 2 hours
customThe cooling bath was removed
stirringstirring
waitwas continued for 3 h
additionthe mixture was diluted with 300 mL ethyl acetate
washwashed with sat. NaHCO3, brine
dry with materialdried over Na2SO4
customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

Sources & evidence

ORD record: ord-f466dc70f6664a43a2e59685051e375f
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084155B2

Linked notes

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