2-Chloro-3-pyridinecarboxaldehyde → 2-((4-Chlorophenyl)sulfonyl)nicotinaldehyde

HRID 874700Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-3-pyridinecarboxaldehyde g, 35.0 mmol) and 4-chlorobenzenesulfinic acid sodium salt (7.75 g, 38.8 mmol) were dissolved in DMSO (120 ml) and the mixture was heated at 100° C. for 72 b under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 85.1 g of crude material. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.62 g (61%) of the desired product as a white powdery solid (MP=100.5-101° C.; IR=1698 cm−1; HPLC 8:00 min>99%).

Workup

temperatureUpon cooling to ambient the mixture
extractionextracted with EtOAc (3×)
washThe combined organics were washed with water, brine
dry with materialdried (MgSO4)
customevaporated to dryness
customto afford 85.1 g of crude material
customThe crude compound was pre-absorbed onto silica
custompurified
customby dry pad suction column chromatography
washeluting with heptane using an EtOAc gradient

Sources & evidence

ORD record: ord-ea9ac2d7c72c4e1c93368752b73a1211
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980927B2

Reaction notes

Loading…