Isopropyl iodide → HCID 66886284, compound

HRID 604925Notes

Reaction equation

HRID 604925 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:19]([CH3:21])[CH3:20].[CH3:22][C:23]1[N:24]=[CH:25][NH:26][CH:27]=1>C(#N)C>[CH:19]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:26]1[CH:27]=[C:23]([CH3:22])[N:24]=[CH:25]1)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 692642-Chloro-5-nitrophenolHCID 178418800HCID 178418800, compound

Product 1

HCID 66886284HCID 66886284, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.0 g (11.5 mmol) 2-chloro-5-nitrophenol in 15 ml of acetonitrile was treated with 11.26 g (34.6 mmol) cesium carbonate and 2.06 g (12.1 mmol) 2-iodopropane and heated overnight at reflux temperature. 993 mg (12.1 mmol) of 4-methylimidazole was added and the mixture refluxed again overnight. After evaporation of the solvent, water was added and the crude material extracted with ethyl acetate. The product was purified on silica gel with ethyl acetate to give 337 mg (11%) of 1-(2-isopropoxy-4-nitro-phenyl)-4-methyl-1H-imidazole as a slightly brownish solid. MS ISP (m/e): 262.0 (100) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.95-7.85 (m, 3H), 7.40 (d, 1H), 6.99 (s, 1H), 4.73 (sept, 1H), 2.31 (s, 3H), 1.40 (d, 6H).

Workup

  1. temperatureheated overnight
  2. temperatureat reflux temperature
  3. temperaturethe mixture refluxed again overnight
  4. customAfter evaporation of the solvent, water
  5. additionwas added
  6. extractionthe crude material extracted with ethyl acetate
  7. customThe product was purified on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-85fffba9660642af8a5d993147d00fe5
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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