Iodoethane → Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate

HRID 2383162Notes

Reaction equation

HRID 2383162 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:20]2[C:24]([CH3:25])=[N:23][N:22]=[N:21]2)=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])(=[O:9])[CH3:8].I[CH2:27][CH3:28]>CC(C)=O>[C:7]([O:10][C:11]1[CH:12]=[CH:13][C:14]([N:20]2[C:24]([CH3:25])=[N:23][N:22]=[N:21]2)=[C:15]([CH:19]=1)[C:16]([O:18][CH2:27][CH3:28])=[O:17])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 670509905-Acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid

Product 1

HCID 67051123Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoateYield 92.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Cesium carbonate (176 g, 1.13 mol) was added to a solution of 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoic acid (164 g, 0.620 mol) in 1.8 L of acetone. The mixture was stirred vigorously and iodoethane (116 g, 0.682 mol) diluted with 100 mL of acetone was added dropwise over a one-hour period. The reaction was stirred overnight at ambient temperature and was then concentrated under reduced pressure. The resulting solid was partitioned between dichloromethane and water. The aqueous fraction was extracted with dichloromethane and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated to give 166 g of ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate as a brown oil.

Workup

  1. additionwas added dropwise over a one-hour period
  2. stirringThe reaction was stirred overnight at ambient temperature
  3. concentrationwas then concentrated under reduced pressure
  4. customThe resulting solid was partitioned between dichloromethane and water
  5. extractionThe aqueous fraction was extracted with dichloromethane
  6. dry with materialthe combined organic fractions were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-779eeb625e844e89bb8488d34927c329
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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