Cesium carbonate → HCID 58122461, compound

HRID 1855535Notes

Reaction equation

HRID 1855535 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:12][C:13]1[N:14]=[CH:15][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])[CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 83315Benzene, 1-chloro-2-methyl-4-nitro-HCID 178418800HCID 178418800, compound

Product 1

HCID 58122461HCID 58122461, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-5-nitro-toluene (2.0 g, 12 mmol), of 4-methylimidazole (1.0 g, 12 mmol) and of cesium carbonate (5.7 g, 17.5 mmol) in acetonitrile (20 mL) was refluxed for 15 h. The reaction mixture was cooled, quenched by addition of water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated under reduced pressure and the crude material was purified by column chromatography on silica gel using ethyl acetate as eluent to yield the title compound (1.27 g, 50%) as a slightly brownish solid. MS ISP (m/e): 218.3 (100) [(M+H)+].

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched by addition of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customthe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f5a55bb8bd3748b3b59f7050b07de2dc
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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