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

HRID 576840Notes

Reaction equation

HRID 576840 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-203113637adb4a7c99af4f8a83a6124e
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

Loading…