Diisopropylcarbodiimide → N-(2-Chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propionamide

HRID 902723Notes

Reaction equation

HRID 902723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([OH:11])=O.[Cl:13][C:14]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].C(N=C=NC(C)C)(C)C>ClC(Cl)C>[Cl:13][C:14]1[C:21]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:9](=[O:11])[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:12]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 126365742-(2-Chlorophenyl)propanoic acid

Product 1

HCID 69254638N-(2-Chloro-3-trifluoromethylbenzyl)-2-(2-chlorophenyl)propionamideYield 37%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 2-(2-chlorophenyl)propionic acid (350 mg, 1.9 mmole) and 2-chloro-3-trifluoromethylbenzylamine (398 mg, 1.9 mmole) in 5 mL of dichloroethane was treated with diisopropylcarbodiimide (0.3 mL, 1.9 mmole) and the reaction was stirred for 16 hours. The solvent was removed, and the residue taken up in Et2O. The Et2O was washed with H2O, 0.1N HCl, and aqueous Na2CO3, dried and the solvent removed. Recrystallization from a mixture of CH2Cl2 and hexane gave the titled compound, 265 mg (37% yield). MS (ESI) 376 (MH+).

Workup

  1. customThe solvent was removed
  2. washThe Et2O was washed with H2O, 0.1N HCl, and aqueous Na2CO3
  3. customdried
  4. customthe solvent removed
  5. customRecrystallization
  6. additionfrom a mixture of CH2Cl2 and hexane

Sources & evidence

ORD record
ord-f9132ed3f7b5427d963d1d8c9436b970
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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