2-(4-Chlorophenyl)ethylamine → N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamide

HRID 1927740Notes

Reaction equation

HRID 1927740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([Cl:20])=[C:22]([N+:30]([O-:32])=[O:31])[CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 4810824N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Chlorophenyl)ethanamine (2.3 ml, 16 mmol) was diluted with DCM (40 mL) followed by the addition of DIEA (2.9 ml, 16 mmol) and 4-chloro-3-nitrobenzoyl chloride (3.0 g, 14 mmol) dropwise in 10 mL of DCM. After stirring for 30 minutes the reaction was loaded directly onto a silica gel column and eluted with hexanes:ethyl acetate (2:1) to yield N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamide (4.0 g, 86% yield) as a white solid.

Workup

  1. washeluted with hexanes:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2c76ef24a03a4efaaffee36308d14c3d
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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