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

HRID 2197847Notes

Reaction equation

HRID 2197847 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-fd21e86055e24bb3949a122569a14670
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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