Pyridine → HCID 10593784, compound

HRID 1451101Notes

Reaction equation

HRID 1451101 reaction equation
[CH2:1]1[S:17][CH:5]([C:6]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]=2[NH2:16])[S:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCOC(C)=O.CCCCCC>ClCCl>[CH2:3]1[S:4][CH:5]([C:6]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]=2[NH:16][S:25]([CH3:24])(=[O:27])=[O:26])[S:17][CH2:1][CH2:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 54147768HCID 54147768, compound

Product 1

HCID 10593784HCID 10593784, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-amino-5-(methoxycarbonyl)benzaldehyde trimethylene mercaptal (Gassman, P. G.; Drews, H. R. J. Am. Chem. Soc. 1978, 100, 7600-7610) (5.0 g, 0.019 mol) in dichloromethane (90 mL) was added pyridine (4.51 mL, 0.055 mol). Methanesulfonyl chloride (4.31 mL, 0.055 mol) was then added over a 5-min period and the reaction mixture heated at reflux overnight. Thin-layer chromatography analysis (SiO2, EtOAc:hexane 1:1) showed the disappearance of the starting material along with the appearance of a new lower-running spot (Rf =0.56) indicating the reaction was complete. Upon cooling, the reaction was washed thoroughly with 10% acetic acid followed by water. The organic layer was dried (Na2SO4), filtered, and concentrated. The crude residue was placed on a SiO2 column and eluted with 1:1 EtOAc:hexane. Fractions containing the desired product were combined and concentrated to yield 5.0 g (77%) of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde trimethylene mercaptal as a yellow solid. An analytical sample, mp 168°-168.5° C. was recrystallized from ethanol.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux overnight
  3. temperatureUpon cooling
  4. washthe reaction was washed thoroughly with 10% acetic acid
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted with 1:1 EtOAc
  9. additionFractions containing the desired product
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5f107e12286a4ae09abb54a068b31f3b
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

Loading…