Dimethyl Sulfoxide → N-(3-Formylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392429Notes

Reaction equation

HRID 392429 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[CH:14]=[C:15]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1.N#N.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)C>[CH:12]([C:13]1[CH:14]=[C:15]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1)=[O:11]

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 947NitrogenHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 23521701n-(3-Hydroxymethylphenyl)-n-(ethylsulfonyl)pyrid-3-ylmethylamine

Product 1

HCID 23521699N-(3-Formylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamineYield 5.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a −78° C. solution of DMSO (20.8 mL, 0.269 mole, 3.1 eq) in DCM (460 mL) was added oxalyl chloride (16 mL, 0.109 mole, 1.25 eq) dropwise and stirred for 15 minutes. N-(3-(Hydroxymethyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (26.4 g, 0.86 mole, 1 eq) was added dropwise via addition funnel as a solution in DCM (146 mL). The reaction mixture was stirred for 30 min. then TEA (102 mL, 1 mole, 11.7 eq) was added via addition funnel. The reaction mixture was allowed to warmed to 0° C. with an ice bath and stirred for 1 hour with a N2 sweep through a bleach/caustic scrubber. The reaction mixture was poured into saturated NaHCO3 and diluted with diethyl ether (2000 mL). The layers were separated and the aqueous layer backextracted with diethyl ether (1000 mL). The combined organics were washed with brine (1000 mL), dried with MgSO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 1:1 DCM/EtOAc to give the title compound as a white solid (15.0 g, 57.2).

Workup

  1. stirringThe reaction mixture was stirred for 30 min.
  2. customThe layers were separated
  3. washThe combined organics were washed with brine (1000 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 1:1 DCM/EtOAc

Sources & evidence

ORD record
ord-c11d95ab345a4fae8c2ff97a29698eaf
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

Loading…