Methanol → 5-(methylthio)-2-(5-phenyl-1H-imidazol-1-yl)pyridine

HRID 1523268Notes

Reaction equation

HRID 1523268 reaction equation
[CH:1](=[N:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([CH2:27][N+:28]#[C-:29])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CO>O.C(COC)OC>[CH3:16][S:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:29][N:28]=[CH:27]2)=[N:10][CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86694680N-benzal-5-(methylthio)pyridine-2-amine

Product 1

HCID 866946815-(methylthio)-2-(5-phenyl-1H-imidazol-1-yl)pyridineYield 50.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-benzal-5-(methylthio)pyridine-2-amine (200 g), tosylmethyl isocyanide (255 g), potassium carbonate (255 g), methanol (3 L) and dimethoxyethane (2 L) were refluxed overnight. The reactant was cooled to room temperature, 10 L water was added and extracted with ethyl acetate. The organic phase was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. The solvent was removed by filtration and reducing pressure. The crude product was purified by column chromatography to obtain the brown solid target compound (118 g, 50% yield). 1H-NMR (300 MHz, CDCl3): δ 2.52 (3H, s), 6.74-6.77 (1H, dd), 7.18-7.22 (3H, m), 7.30-7.33 (3H, m), 7.45-7.48 (1H, dd), 8.05-8.05 (1H, d), 8.38-8.39 (1H, d). LC-MS m/z: 268 [M++1].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated NaCl solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was removed by filtration
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e634881782c449e88e539f8b29bf4559
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

Loading…