Isopropyl iodide → 5-(4-Benzyloxyphenyl)-2-isopropyl-2H-tetrazole

HRID 423255

Reaction equation

HRID 423255 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:22](I)([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]=[N:18][N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 47709095-[4-(benzyloxy)phenyl]-2H-tetrazole

Product 1

HCID 586297825-(4-Benzyloxyphenyl)-2-isopropyl-2H-tetrazoleYield 97.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Benzyloxyphenyl)-2H-tetrazole (500 mg) was added to a suspension of sodium hydride (96 mg) in dimethylformamide (5 mL) under ice-cooling. The mixture was stirred at room temperature for 0.5 hour. After addition of isopropyl iodide (405 mg) thereto, the mixture was stirred at 60° C. for 2 hours under heating. The reaction mixture was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed with water and saturated brine, dried anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1, v/v) to give the title compound (571 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. temperatureunder heating
  4. temperaturefor cooling down to room temperature
  5. washwashed with water and saturated brine, dried anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-f91d6be9cbca49738da14158e811620d
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Linked notes

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