Bis(2-Methoxyethyl)amine → N,N-bis(2-methoxyethyl)-3-nitrobenzamide

HRID 564947Notes

Reaction equation

HRID 564947 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].C(N(CC)CC)C.[N+:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([O-:19])=[O:18]>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][CH3:9])[C:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=1

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 22113236N,N-bis(2-methoxyethyl)-3-nitrobenzamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N-bis(2-methoxyethyl)amine (2.40 g) and triethylamine (2.27 g) in dichloromethane (30 ml) was added 3-nitrobenzoyl chloride (2.78 g) in an ice-water bath. The mixture was stirred at ambient temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution, water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified with column chromatography eluting with dichloromethane-methanol to give N,N-bis(2-methoxyethyl)-3-nitrobenzamide (4.12 g) as an oil.

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified with column chromatography
  5. washeluting with dichloromethane-methanol

Sources & evidence

ORD record
ord-4f71bcd2f4224fd392b432a4268c675a
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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