p-Toluidine → 4-Chloro-N-(4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 2353363Notes

Reaction equation

HRID 2353363 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.CCN(CC)CC.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]=1[C:26]([F:29])([F:28])[F:27]>C(Cl)Cl>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[O:22])=[CH:19][C:18]=1[C:26]([F:27])([F:28])[F:29]

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 36996914-Chloro-3-(trifluoromethyl)benzoyl chloride

Product 1

HCID 684512324-Chloro-N-(4-methylphenyl)-3-(trifluoromethyl)benzamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of p-toluidine (0.44 g, 4.1 mmol) in 10 ml of CH2Cl2 (pre-cooled to 0° C.) are added Et3N (1.14 ml, 2 eq.) and 4-chloro-3-trifluoromethyl-benzoyl chloride (1 g, 4.1 mmol) in 5 ml of CH2Cl2. The mixture is slowly warmed to room temperature and continued to stir at room temperature for an hour. The mixture is diluted with 50 ml of CH2Cl2, washed with 1N HCl solution, and brine. The organic layer is separated, dried over MgSO4, filtered, and concentrated. The residue is purified by column chromatography (EtOAc/Hexanes, 2:3) to give 1.25 g (97%) of 4-chloro-N-p-tolyl-3-trifluoromethyl-benzamide.

Workup

  1. washwashed with 1N HCl solution, and brine
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography (EtOAc/Hexanes, 2:3)

Sources & evidence

ORD record
ord-913f2576eafb4c48a3b97c32da571193
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

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