Potassium Carbonate → N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide

HRID 72753Notes

Reaction equation

HRID 72753 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[S:16]1[CH:20]=[CH:19][C:18]([C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)=[CH:17]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>[Cl-].[Na+].O>[CH3:9][N:8]([CH3:10])[C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([N:25]2[CH:24]=[CH:23][N:22]=[C:21]2[C:18]2[CH:19]=[CH:20][S:16][CH:17]=2)=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 197764582-(3-thienyl)-1H-imidazoleHCID 252393174-fluoro-N,N-dimethyl-3-nitrobenzamide

Product 1

HCID 59198669N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoro-N,N-dimethyl-3-nitrobenzamide 1.06 g, 2-(3-thienyl)-1H-imidazole as synthesized in above Production Example 2, 747 mg, potassium carbonate 1.37 g and N,N-dimethylacetamide 10 mL were mixed, and its outside temperature was heated to 100° C. for 6.5 hours. The reaction liquid was poured into brine and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. Distilling the solvent off, 1.30 g of the title compound was obtained.

Workup

  1. additionwere mixed
  2. customThe reaction liquid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationDistilling the solvent off, 1.30 g of the title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-4f4a683cb50b43479e6034c99e66f519
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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