Methyl iodide → HCID 19612501, compound

HRID 1607576Notes

Reaction equation

HRID 1607576 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:11][N:10]=[N:9][N:8]=2)[CH:2]=1.[OH-].[Na+].[CH3:14]I>C(O)C>[CH3:14][N:9]1[N:10]=[N:11][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178420778HCID 178420778, compound

Product 1

HCID 19612501HCID 19612501, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3-pyridyl)-tetrazole (11) (J. M. McManus and R. M. Herbst, J. Am. Chem. Soc., 24 (1959) 1462-64) (10 g, 0.068 mol), sodium hydroxide (2.73 g, 0.068 mol), and methyl iodide (14.5 g, 0.1 mol) in ethanol (100 ml) was stirred at 40° C. overnight. The mixture was filtered and the filtrate was evaporated. The residue was dissolved in dichloromethane (100 ml), and the solution was washed three times with water (100 ml). The organic phase was dried over magnesium sulphate and evaporated yielding 3.21 g (0.020 mol, 30%) of 12 with M.P. 108°-110° C. According to the 1H NMR spectrum the product contained less than 10% of the 1-isomer.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. washthe solution was washed three times with water (100 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-69f7aef8c98242b5bd62be7816e46a00
Source dataset
uspto-grants-1989_09
Patent number
US04866077

Reaction notes

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