2,4,6-Trimethoxybenzaldehyde → (E)-2-methoxy-3-nitro-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)pyridine

HRID 72658Notes

Reaction equation

HRID 72658 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:12][C:13](O)=O)=[O:11])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17].[CH3:19][O:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[C:22]=1C=O>N1C=CC=CC=1.N1CCCCC1>[CH3:1][O:2][C:3]1[C:4]([N+:16]([O-:18])=[O:17])=[CH:5][C:6]([CH2:9][S:10](/[CH:12]=[CH:13]/[C:22]2[C:25]([O:31][CH3:32])=[CH:26][C:27]([O:29][CH3:30])=[CH:28][C:21]=2[O:20][CH3:19])=[O:11])=[CH:7][N:8]=1

Participants

5

Reactant 2

HCID 700192,4,6-TrimethoxybenzaldehydeHCID 67995981HCID 67995981, compound

Product 1

HCID 56598657(E)-2-methoxy-3-nitro-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)pyridineYield 10%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2-((6-methoxy-5-nitropyridin-3-yl)methylsulfinyl)acetic acid (0.15 g, 0.5 mmol) in dry pyridine (20 mL) was treated with 2,4,6-trimethoxybenzaldehyde (0.20 g, 1 mmol) and piperidine (10 drops). The mixture was refluxed for 2-3 hrs. The mixture was evaporated and the residue was purified by flash chromatography; yield 10%; 1H-NMR (CDCl3): δ 3.83 (s, 6H, OCH3), 3.83 (s, 3H, OCH3), 3.89 (1H, CH), 4.07 (1H, CH), 4.09 (s, 3H, OCH3), 6.09 (s, 2H, Ph-H), 6.97 (d, 1H, J=15.2 Hz, CH), 7.28 (d, 1H, J=15.2 Hz, CH), 8.19 (d, 1H, J=2.3 Hz, Py-H), 8.29 (d, 1H, J=2.3 Hz, Py-H). HR-MS (ESI+) m/z 408.8426 C18H20N2O7S requires 408.0991.

Workup

  1. temperatureThe mixture was refluxed for 2-3 hrs
  2. customThe mixture was evaporated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d5e3a9b867dc4d21bd8a50d6f2f332dd
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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