Dicyclohexylcarbodiimide → 2-Chloro-N-[2-(3-trifluoromethoxy-phenylamino)-ethyl]-propionamide

HRID 1096250Notes

Reaction equation

HRID 1096250 reaction equation
[Cl:1][CH:2]([CH3:6])[C:3](O)=[O:4].[F:7][C:8]([F:21])([F:20])[O:9][C:10]1[CH:11]=[C:12]([NH:16][CH2:17][CH2:18][NH2:19])[CH:13]=[CH:14][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:1][CH:2]([CH3:6])[C:3]([NH:19][CH2:18][CH2:17][NH:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][C:8]([F:7])([F:20])[F:21])[CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 117342-Chloropropionic acidHCID 629184031,2-Ethanediamine, N1-[3-(trifluoromethoxy)phenyl]-

Product 1

HCID 667831992-Chloro-N-[2-(3-trifluoromethoxy-phenylamino)-ethyl]-propionamideYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloropropionic acid (103 mg, 0.95 mmol) in CH2Cl2 (10 mL) was added dropwise at −30° C. to a solution of N1-(3-trifluoromethoxy-phenyl)-ethane-1,2-diamine (210 mg, 0.95 mmol) and N,N′-dicyclohexylcarbodiimide (226 mg, 1.10 mmol) in CH2Cl2 (20 mL), then after 1 h insoluble material was removed by filtration and the filtrate evaporated. Chromatography (SiO2; heptane/EtOAc 3:2) afforded the title compound (272 mg, 92%). Colorless oil, MS: 309.3 (M−H)−.

Workup

  1. customafter 1 h insoluble material was removed by filtration
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-19f50f92ded04e8f8c88896c9e569bb6
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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