Iodoethane → ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate

HRID 432696Notes

Reaction equation

HRID 432696 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])[N:5]=[N:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](I)[CH3:23]>CC(C)=O.ClCCl>[CH3:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH2:22][CH3:23])=[O:10])[N:5]=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 125241922-(5-methyl-1H-tetrazol-1-yl)benzoic acid

Product 1

HCID 3761737ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoateYield 90.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid (89.7 g, 0.44 mol) was dissolved in acetone (1 L) and cesium carbonate (214.7 g, 0.66 mol) was added with vigorous stirring. Ethyl iodide (70.3 ml, 0.88 mol) was added dropwise and the reaction was heated to reflux for 4 hours. The reaction was cooled to room temperature and filtered. The acetone was removed in vacuo to yield a yellow solid which was dissolved in dichloromethane (800 ml) and washed with saturated sodium bicarbonate (200 ml). The organic fraction was dried (Na2SO4), filtered, and concentrated to yield 92.7 g of ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoate as a light yellow solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. filtrationfiltered
  4. customThe acetone was removed in vacuo
  5. customto yield a yellow solid which
  6. washwashed with saturated sodium bicarbonate (200 ml)
  7. dry with materialThe organic fraction was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e4eb31f9bf1543d98651871e1774795c
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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