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

HRID 2358683Notes

Reaction equation

HRID 2358683 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 6344DichloromethaneSolvent2×

Procedure

The compound from Example 126c (1.0 g, 3.2 mmol) in CH2Cl2 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-968e30add60c4789938946a481dd9ac5
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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