Methyl iodide → HCID 19612501, compound

HRID 1600439Notes

Reaction equation

HRID 1600439 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, compound

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 with water (100 ml). The organic phase wan 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 with water (100 ml)
  5. dry with materialThe organic phase wan dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-ba9897736c6140dfa8ba13c48929a599
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

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