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

HRID 726319Notes

Reaction equation

HRID 726319 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-efcd458ac7034a419d1bd976b3b444b2
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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