Methyl iodide → HCID 14443413, compound

HRID 1721381Notes

Reaction equation

HRID 1721381 reaction equation
CI.[NH:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][N:5]=[N:4]1.[CH2:18](N(CC)CC)C>C(#N)C>[CH3:18][N:6]1[C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)=[N:3][N:4]=[N:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178526616HCID 178526616, compound

Product 1

HCID 14443413HCID 14443413, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl iodide (34.1 ml, 0.5 mol) in acetonitrile (100 ml) was added dropwise, over lh, to a solution of 4-(1H-tetrazol-5-ylmethyl)nitrobenzene (20.5 g, 0.1 mmol), and triethylamine (18.7 ml, 0.25 mol), in acetonitrile (500 ml), at room temperature. The mixture was stirred for 3h, the solvent removed under vacuum and residue dissolved in EtOAc (500 ml). The solution was washed with water (2x) and brine (1x) and the solvent evaporated. The crude product was chromatographed through silica-gel eluting with EtOAc/hexane (1:1)→EtOAc (100%) to give 2 components. The more polar product (7.9 g) was identified as the desired 1-methyl substituted tetrazole. The less polar product (7.0 g) was identified as being the 2-substitution product; 5 (360 MHz, CDCl3, more polar isomer) 3.94 (3H, s, CH3), 4.40 (2H, s, CH2), 7.42 (2H, d, J=8.7 Hz, Ar--H), 8.21 (2H, d, J=8.7Hz, Ar--H).

Workup

  1. customthe solvent removed under vacuum and residue
  2. dissolutiondissolved in EtOAc (500 ml)
  3. washThe solution was washed with water (2x) and brine (1x)
  4. customthe solvent evaporated
  5. customThe crude product was chromatographed through silica-gel
  6. washeluting with EtOAc/hexane (1:1)→EtOAc (100%)
  7. customto give 2 components

Sources & evidence

ORD record
ord-4c8128c483864307b0e5c0f86b37eb68
Source dataset
uspto-grants-1996_04
Patent number
US05510362

Reaction notes

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