Triethylamine → N-(3-Bromo-4-Methylphenyl)-3-(Trifluoromethyl)Benzamide

HRID 1662832Notes

Reaction equation

HRID 1662832 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([C:11]([F:10])([F:21])[F:22])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 58601069N-(3-Bromo-4-Methylphenyl)-3-(Trifluoromethyl)Benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-methylbenzenamine (0.82 g, 4.4 mmol) in anhydrous CH2Cl2 (40 mL) was added 3-(trifluoromethyl)benzoyl chloride (0.72 ml, 4.85 mmol) and triethylamine (2.5 ml, 17.6 mmol). The mixture was stirred overnight at room temperature. The saturated NaHCO3 (80 mL) was added and the mixture was stirred for 5 min. The organic layer was separated and aqueous was extracted with CH2Cl2 (3×20 mL). The combined organic solution was dried (Na2SO4). The solvent was removed in vacuo. The title compound was afforded as a yellow solid (1.48 g, 94%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. customThe organic layer was separated
  3. extractionaqueous was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic solution was dried (Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8abe591edd99402e9437bd66916ede94
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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