2-Methoxy-5-nitropyridine → 6-Methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine

HRID 481096

Reaction equation

HRID 481096 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.Cl[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].CC(C)([O-])C.[K+]>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 795252-Methoxy-5-nitropyridineHCID 5628451-Chloromethanesulfonyl-4-methylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 136265146-Methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridineYield 37.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15.4 g (0.1 mol) of 6-methoxy-3-nitropyridine and 20.4 g (0.1 mol) of 1-chloromethane-sulfonyl-4-methyl-benzene is dissolved in 100 mL of DMF and cooled to 5 C. To this solution is added, dropwise, 100 mL (0.1 mol) of a 1M solution of potassium t-butoxide in THF, keeping the temperature≦10 C. The dark reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is evaporated to remove the THF, and to the remaining solution is added 100 mL of water. A dark brown precipitate formed which is collected by filtration. This solid is triturated with isopropyl ether for 1 hour and refiltered to yield 12 grams of 6-methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine. 1H NMR (CDCl3) δ8.25 (d, 1H), 7.60 (m, 2H), 7.30 (m, 2H), 6.80 (d, 1H), 5.10 (s, 1H), 3.75 (s, 3H), 2.40 (s, 3H). Mass Spectrum: m/e=323.1 (p+1), TLC (CDCl3) Rf=0.45

Workup

  1. temperaturecooled to 5 C
  2. additionTo this solution is added
  3. customThe dark reaction mixture
  4. customThe reaction mixture is evaporated
  5. customto remove the THF
  6. additionto the remaining solution is added 100 mL of water
  7. customA dark brown precipitate formed which
  8. filtrationis collected by filtration
  9. customThis solid is triturated with isopropyl ether for 1 hour

Sources & evidence

ORD record
ord-1baee5421af546d39c44a5a0d9240dac
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Linked notes

Loading…