4-(Trifluoromethyl)aniline → 2,4-dichloro-N-(4-(trifluoromethyl)phenyl)benzamide

HRID 2215057Notes

Reaction equation

HRID 2215057 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(C(C)C)CC)(C)C.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([F:21])([F:30])[F:31])=[CH:24][CH:25]=1)=[O:5]

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 666452,4-Dichlorobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 9564532,4-dichloro-N-(4-(trifluoromethyl)phenyl)benzamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part A: 2,4-Dichlorobenzoyl chloride (40.0 g, 0.19 mol) is dissolved in tetrahydrofuran (1 L). To the resulting stirred solution is successively added diisopropylethylamine (DIPEA) (73.4 mL, 2.2 molar equivalent) and 4-(trifluoromethyl)phenylamine (30.7 g, 0.19 mol). After one hour the mixture is concentrated in vacuo to give an oil. This oil is crystallised from ethanol to give pure 2,4-dichloro-N-(4-(trifluoromethyl)phenyl)benzamide (53.2 g, 83% yield). 1H-NMR (200 MHz, DMSO-d6): δ 10.90 (br s, 1H), 7.91 (br d, J=8 Hz, 2H), 7.63–7.77 (m, 4H), 7.57 (dt, J=8 Hz, J=2 Hz, 1H).

Workup

  1. concentrationAfter one hour the mixture is concentrated in vacuo
  2. customto give an oil
  3. customThis oil is crystallised from ethanol

Sources & evidence

ORD record
ord-f7634b0e63d844c1bb62b9ea51a12d59
Source dataset
uspto-grants-2006_09
Patent number
US07109216B2

Reaction notes

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