HCID 58122461, compound → HCID 58122362, compound

HRID 1855536Notes

Reaction equation

HRID 1855536 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[CH3:16])[CH:6]=1>C(OCC)(=O)C.C(O)C>[CH3:16][C:8]1[CH:9]=[C:10]([NH2:13])[CH:11]=[CH:12][C:7]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1

Participants

4

Reactant 1

HCID 58122461HCID 58122461, compound

Product 1

HCID 58122362HCID 58122362, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methyl-1-(2-methyl-4-nitro-phenyl)-1H-imidazole (1.26 g, 5.8 mmol) and of stannous chloride dihydrate (6.81 g, 30.2 mmol) in ethyl acetate (40 mL) and ethanol (20 mL) was stirred for 1 hour at 70° C. The reaction mixture was quenched by addition of water, neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give the crude title compound (1.08 g, 99%) as a yellowish gum. MS ISP (m/e): 188.4 (100) [(M+H)+].

Workup

  1. customThe reaction mixture was quenched by addition of water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f7fb97dbb8054f69ab74fafb278d1e6e
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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