Methyl iodide → HCID 69521177, compound

HRID 856689Notes

Reaction equation

HRID 856689 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:17](=O)([O-])[O-].[K+].[K+].I[CH3:24]>C(#N)C>[CH3:17][N:13]1[C:12]([CH2:11][S:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:16][N:15]=[N:14]1.[CH3:24][N:14]1[N:15]=[N:16][C:12]([CH2:11][S:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:13]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178526720HCID 178526720, compound

Product 2

HCID 69521177HCID 69521177, compoundHCID 69522097HCID 69522097, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole (6.3 g) were added acetonitrile (315 ml), and then, to this solution was added potassium carbonate (4.5 g) and iodomethane (1.75 ml), and the mixture was stirred for 240 hours at room temperature. The solvent was removed under reduced pressure, and to the obtained residue was added ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 1-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole and 2-methyl-5-[[(4-nitrophenyl)sulfanyl]methyl]-1,2,3,4-tetrazole as mixture (3.87 g, 1:1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionto the obtained residue was added ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-b615ebe8b6f545dfaaec27b2d7b88108
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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