4-Chlorobenzylamine → HCID 86600612, compound

HRID 859848Notes

Reaction equation

HRID 859848 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:11]([CH3:15])[C:12]([OH:14])=O)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:12](=[O:14])[C:11](=[N:10][NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:16])=[CH:8][CH:7]=2)[CH3:15])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 85847975HCID 85847975, compound

Product 1

HCID 86600612HCID 86600612, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Trifluoromethylphenyl hydrazono) propionic acid (0.74 g, 3.0 mmol) was dissolved in dichloromethane (15 ml), and 4-chlorobenzyl amine (0.42 g, 3.0 mmol) and 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloric acid salt (0.58 g, 3.0 mmol) were added thereto. 20 hours later, the mixture was washed with 1N hydrochloric acid, a saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate and then filtrated. The residue obtained by concentrating the resulting filtrate was suspended in a mixed solvent of hexane and chloroform (1:1) and filtered to obtain N-(4-chlorobenzyl)-2-(4-trifluoromethylphenyl hydrazono) propionic acid amide (Compound No. 62) (0.83 g, 2.2 mmol, 75%).

Workup

  1. wash20 hours later, the mixture was washed with 1N hydrochloric acid
  2. dry with materiala saturated sodium bicarbonate water and a saturated brine, and dried on sodium sulfate
  3. filtrationfiltrated
  4. customThe residue obtained
  5. concentrationby concentrating the resulting filtrate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cc642048ca904a92b76511e93699603f
Source dataset
uspto-grants-2006_12
Patent number
US07153815B2

Reaction notes

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