Cesium carbonate → HCID 58122461, compound

HRID 2075977Notes

Reaction equation

HRID 2075977 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 overnight. The reaction mixture was cooled, quenched by addition of water and extracted with ethyl acetate. The solvent was removed 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. customThe solvent was removed under reduced pressure
  5. customthe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-65769289cfb543c6a4bd3fe80c233fad
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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