Diisopropylethylamine → N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide

HRID 412716Notes

Reaction equation

HRID 412716 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH2:8].C(N(C(C)C)CC)(C)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])[C:27](Cl)=[O:28]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH:8][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:32]([N+:33]([O-:35])=[O:34])=[C:24]([O:23][CH3:22])[CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 18537879N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

A mixture comprising 2-(2-methoxyphenoxy)ethylamine (10 g, 59.9 mmol), diisopropylethylamine (13.9 mL, 81.6 mmol) and dichloromethane (80 mL) was cooled to 0° C. and then a solution of 3-methoxy-4-nitrobenzoyl chloride (11.76 g, 54.4 mmol) in dichloromethane (50 mL) was added dropwise. The mixture was allowed to warm to 23° C. over two hours, quenched with aqueous hydrochloric acid (3M, 20 mL), washed with water (3×20 mL), dried (Na2SO4) and concentrated in vacuo to provide N-[2-(2-methoxyphenoxy)ethyl]-3-methoxy-4-nitrobenzamide (14 g, 74% yield) an off white solid; MS (PB-PCI) C17H18N2O6 m/e calc 346.34; found 347 (MH+).

Workup

  1. customquenched with aqueous hydrochloric acid (3M, 20 mL)
  2. washwashed with water (3×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13b6b1e0da87449e8ece675cecb01652
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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