Methyl iodide → HCID 22677389, compound

HRID 1837448Notes

Reaction equation

HRID 1837448 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[C:4]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[N:3]=1.I[CH3:16].[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[C:4]([C:10]2[N:14]([CH3:17])[N:13]=[N:12][N:11]=2)[N:3]=1.[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[C:4]([C:10]2[NH:14][N:13]([CH3:16])[NH:12][N:11]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178477920HCID 178477920, compound

Product 2

HCID 22677389HCID 22677389, compoundHCID 22677452HCID 22677452, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,3,4-trichloro-6-(1H-tetrazol-5-yl)pyridine (3.25 g, 13 mmol), iodomethane (1.84 g, 13 mmol), and potassium carbonate (1.79 g, 13 mmol) in dimethylformamide (100 mL) was stirred at 25° C. for 22 hours. The volatiles were removed and the residue purified by column chromatography (15% ethyl acetate in hexane) to provide 2,3,4-trichloro-6-(1-methyl-1H-tetrazol-5-yl)pyridine (1.66 g, 6.3 mmol), mp 138-141° C. and 2,3,4-trichloro-6-(2-methyl-1H-tetrazol-5-yl)pyridine (1.05 g, 4.0 mmol), mp 156-157° C.

Workup

  1. customThe volatiles were removed
  2. customthe residue purified by column chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1ca300d49d7e436cbfd1743bd9385371
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

Loading…