Methanol → HCID 67994783, compound

HRID 72647Notes

Reaction equation

HRID 72647 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6]([O:9][CH3:10])=[N:7][CH:8]=1.C(O[CH2:18][SH:19])(=O)C.[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].[CH3:26]O>>[CH3:10][O:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][S:19][CH2:18][C:20]([O:21][CH3:26])=[O:23])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 15354425Mercaptomethyl acetateHCID 67995475HCID 67995475, compound

Product 1

HCID 67994783HCID 67994783, compoundYield 73%

Procedure

To a solution of 5-bromomethyl-2-methoxy-3-nitropyridine (4.92 g, 0.02 mol) in methanol (50 mL), mercaptomethyl acetate (2.7 mL, 0.03 mol) and sodium carbonate (2.12 g, 0.02 mol) were added at room temperature and stirred for 1 h. After evaporated to dryness, the mixture was dissolved in ethyl acetate (200 mL), filtered and concentrated under reduced pressure. Recrystallisation from EtOH (50 mL) gave the pure product as a pale green solid (3.99 g, 73%). M.p. 57-60° C.; 1H-NMR (DMSO-d6): δ 3.32 (s, 2H, CH2), 3.59 (s, 3H, OCH3), 3.90 (s, 2H, CH2), 4.03 (s, 3H, OCH3), 8.42 (d, 1H, J=2.0 Hz, Py-H), 8.44 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (DMSO-d6): δ 31.62, 32.60, 52.54, 55, 17, 128.35, 133.77, 136.05, 152.14, 155.16, 170.74; HR-MS (ESI+) m/z: 273.0573 [M+H]+; C7H6N2O3 requires 272.0467.

Workup

  1. customAfter evaporated to dryness
  2. dissolutionthe mixture was dissolved in ethyl acetate (200 mL)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallisation from EtOH (50 mL)

Sources & evidence

ORD record
ord-12adb15758e74b5d8fd440ccd761789b
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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