Isopropyl iodide → HCID 19884287, compound

HRID 846870Notes

Reaction equation

HRID 846870 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:17](=[O:18])[NH:16][N:15]=[N:14]1)([CH3:3])[CH3:2].[CH:19](I)([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[N:13]1[C:17](=[O:18])[N:16]([CH:19]([CH3:21])[CH3:20])[N:15]=[N:14]1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 136133797HCID 136133797, compound

Product 1

HCID 19884287HCID 19884287, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.3 g of 1-(2,6-diisopropylphenyl)-5-oxo-2-tetrazoline, 12.8 g of isopropyl iodide and 10.4 g of pulverised potassium carbonate are dissolved in 140 ml of dimethylformamide and stirred for 2 hours at +60° C. The resulting suspension is poured onto water and extracted three times with ether. The combined ethereal phases are washed with water and saturated sodium chloride solution, dried over Na2SO4 and concentrated by evaporation. In order to remove the 1-(2,6-diisopropylphenyl)-5-isopropoxy-tetrazole formed as by-product, the mixture is chromatographed on silica gel with the eluant CH2Cl2 /cyclohexane (3:1). In this manner 8.7 g of 1-(2,6-diisopropylphenyl)-4-isopropyl-5-oxo-2-tetrazoline having a melting point of 60°-62° C. are obtained.

Workup

  1. additionThe resulting suspension is poured onto water
  2. extractionextracted three times with ether
  3. washThe combined ethereal phases are washed with water and saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. customIn order to remove the 1-(2,6-diisopropylphenyl)-5-isopropoxy-tetrazole
  7. customformed as by-product
  8. customthe mixture is chromatographed on silica gel with the eluant CH2Cl2 /cyclohexane (3:1)

Sources & evidence

ORD record
ord-4dc41a392b3f4eb1b34289ec13024786
Source dataset
uspto-grants-1992_08
Patent number
US05138068

Reaction notes

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