Triethylamine → 3-amino-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamide

HRID 1968421Notes

Reaction equation

HRID 1968421 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[C:14]([F:17])([F:16])[F:15])[CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.[CH3:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][C:27]=1[N+:35]([O-])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:35][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:26]=1[CH3:25])[C:30]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[C:8]([C:14]([F:17])([F:15])[F:16])[CH:9]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 549354784-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)aniline

Product 1

HCID 598224523-amino-4-methyl-N-[4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenyl]-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-methyl-imidazol-1-yl)-3-trifluoromethyl-phenylamine (1.0 g, 4.15 mmol), triethylamine (1.74 mL, 12.5 mmol) in anhydrous CH2Cl2 (60 mL) at 0° C. is added 4-methyl-3-nitro-benzoyl chloride (660 μL, 4.57 mmol) dropwise. After stirring for 2 hours at room temperature, the reaction mixture is poured into 100 mL CH2Cl2 and 50 mL saturated NaHCO3 solution with rapid stirring. After 10 minutes, the mixture is partitioned in a separator funnel and extracted three times with 100 mL CH2Cl2. The organic extracts are washed with brine, and dried over MgSO4. Filtration and concentration under reduced pressure, afforded the desired compound, which is used in the next step without any further purification.

Workup

  1. waitAfter 10 minutes
  2. customthe mixture is partitioned in a separator funnel
  3. extractionextracted three times with 100 mL CH2Cl2
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-220f2707f3a74672b89befff12ba9a68
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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