Bis(2-Methoxyethyl)amine → HCID 21272461, compound

HRID 1193539Notes

Reaction equation

HRID 1193539 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH3:16][O:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][O:23][CH3:24].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:16][O:17][CH2:18][CH2:19][N:20]([CH2:21][CH2:22][O:23][CH3:24])[C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 2383Bis(2-Methoxyethyl)amineHCID 118802,4-Dinitrobenzoic acidHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 21272461HCID 21272461, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of 212.0 g of 2,4-dinitrobenzoic acid in 900 ml of toluene were added with stirring 101.0 g of triethylamine, followed by 159.6 g of bis(2- methoxyethyl)amine. Next 75.7 g of phosphorus oxychloride was added dropwise at such a rate to maintain the reaction temperature below 90° C. The mixture was refluxed for 5 hrs, cooled to 80° C., and poured slowly into 1000 ml of aqueous 5% NaHCO3 solution with stirring. The precipitate was filtered, washed with water and recrystallized from hot methanol to yield 250.7 g of N,N-bis(2-methoxyethyl)-2,4-dinitrobenzamide, mp 89° C. An additional 19.0 g of material was recovered from the toluene filtrate.

Workup

  1. temperatureto maintain the reaction temperature below 90° C
  2. temperatureThe mixture was refluxed for 5 hrs
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customrecrystallized from hot methanol

Sources & evidence

ORD record
ord-b826f6a4e372404fb12c76f900ec0d8e
Source dataset
uspto-grants-1989_03
Patent number
US04810769

Reaction notes

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