Methyl iodide → 4-(4-Cyclopropyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 639781Notes

Reaction equation

HRID 639781 reaction equation
I[CH3:2].[CH:3]1([N:6]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[N:9][N:8]=[C:7]2[SH:17])[CH2:5][CH2:4]1>C(O)C.[OH-].[Na+]>[CH:3]1([N:6]2[C:7]([S:17][CH3:2])=[N:8][N:9]=[C:10]2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178527957HCID 178527957, compound

Product 1

HCID 578379714-(4-Cyclopropyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)-pyridineYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of iodomethane (0.457 mL, 7.33 mmol) in ethanol (3 mL) was added to a solution of 4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (1 g, 4.58 mmol) in 1M sodium hydroxide (10 mL) at room temperature. After stirring overnight, the reaction mixture was extracted with dichloromethane and then the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the titled compound (729.1 mg, 69%, beige solid). 1H NMR (CDCl3) δ (ppm): 8.77 (d, 2H), 7.75 (m 2H), 3.23 (m, 1H), 2.82 (s, 3H), 1.17 (m, 2H), 0.80 (m, 2H).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d978c16376ea4dd9949a471f86faa2f1
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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