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

HRID 1168562Notes

Reaction equation

HRID 1168562 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-].[K+].[K+].I[CH2:23][CH3:24]>CC(C)=O>[CH2:23]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[N:6]1[C:2]([CH3:1])=[N:3][N:4]=[N:5]1)[CH3:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 125241922-(5-methyl-1H-tetrazol-1-yl)benzoic acid

Product 1

HCID 3761737ethyl 2-(5-methyl-1H-tetrazol-1-yl)benzoateYield 87.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (3.2 L) and 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid (228 g) were combined then stirred at ambient temperature for 15 minutes. Potassium carbonate (228 g) was added to the reaction mixture in a single portion. Iodoethane (366.8 g) was added dropwise to the reaction mixture producing a slight exotherm. The reaction mixture was heated at reflux for about 4 hours then stirred overnight while cooling to ambient temperature. The precipitated salts were removed by filtration then rinsed with acetone. The combined filtrates were evaporated under vacuum. The residue was dissolved in dichloromethane (1.5 L). The dichloromethane solution was washed with water (1.5 L), dried over magnesium sulfate then concentrated under vacuum to provide 227 g of ethyl-2-(5-methyl-1H-tetrazol-1-yl)benzoate as a white solid m.p. 98-100° C.

Workup

  1. customproducing a slight exotherm
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for about 4 hours
  4. customThe precipitated salts were removed by filtration
  5. washthen rinsed with acetone
  6. customThe combined filtrates were evaporated under vacuum
  7. dissolutionThe residue was dissolved in dichloromethane (1.5 L)
  8. washThe dichloromethane solution was washed with water (1.5 L)
  9. dry with materialdried over magnesium sulfate
  10. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-2c12814be6e74c5db974adbe5dc097d8
Source dataset
uspto-grants-2003_09
Patent number
US06624305B2

Reaction notes

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