2-Methoxyethylamine → 4-(4-chloro-2-nitrophenoxy)-N-(2-methoxyethyl)benzamide

HRID 883898Notes

Reaction equation

HRID 883898 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][O:22][CH2:23][CH2:24][NH2:25]>C(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH:25][CH2:24][CH2:23][O:22][CH3:21])=[O:12])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 866154944-(4-Chloro-2-nitrophenoxy)benzoyl chloride

Product 1

HCID 259313144-(4-chloro-2-nitrophenoxy)-N-(2-methoxyethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound from Example 34c (1.0 g, 3.2 mmol) in CH2Cl, was added to a mixture of 2-methoxyethanamine (722 mg, 9.61 mmol) in CH2Cl2. Mixture was stirred for 12 hours. Mixture was concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 50% EtOAc/hexane giving the title compound as a yellow oil (1.1 g, 100%).

Workup

  1. concentrationMixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0eb19f933332488b99aa77dee45322bd
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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