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

HRID 1055662Notes

Reaction equation

HRID 1055662 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[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>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][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:6]=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.51 g (29.6 mmol) of 3-bromo-4-methylaniline were dissolved in 127 ml of dichloromethane, 6.18 g (29.6 mmol) of 3-(trifluoromethyl)benzoyl chloride and 4.54 ml (32.6 mmol) of triethylamine were added and the mixture was stirred at RT for 30 min. All volatile components were removed under reduced pressure and the residue was suspended in 50 ml of methanol. The solid was filtered off and the filtrate was stirred into 100 ml of 1 M hydrochloric acid. The precipitate formed was filtered off, washed with water and dried. This gave 7.05 g (90% pure, 60% of theory) of the title compound.

Workup

  1. customAll volatile components were removed under reduced pressure
  2. filtrationThe solid was filtered off
  3. stirringthe filtrate was stirred into 100 ml of 1 M hydrochloric acid
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-0a54c400b4194e0e90bcf94592d2fd08
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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