Ethylene Glycol → HCID 53870986, compound

HRID 434474Notes

Reaction equation

HRID 434474 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH3:15])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C(O)C>[O:19]1[CH2:20][CH2:1][O:2][CH:3]1[CH2:4][NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH3:15])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 20492566N-(2,2-Dimethoxyethyl)-4-methyl-2,6-dinitroaniline

Product 1

HCID 53870986HCID 53870986, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

N-(2,2-dimethoxyethyl)-2,6-dinitro-4-methylaniline (3.0 grams; 0.0105 mole), ethylene glycol (0.65 grams; 0.0105 mole), p-toluenesulfonic acid (200 mg) and ethanol solvent were placed in a glass reaction vessel equipped with a stirrer heating mantle and thermometer. The reaction mixture was heated to 110° C. and maintained at that temperature with stirring for one hour. Then the reaction mixture was cooled to room temperature, ethyl acetate has added and the mixture was washed with water and sodium bicarbonate solution. The solution was dried over anhydrous magnesium sulfate and evaporated to yield the desired product (2.0 grams) of a yellow oil. The product was analyzed for C11H10N3O6 :

Workup

  1. customequipped with a stirrer
  2. temperatureheating mantle and thermometer
  3. temperaturemaintained at that temperature
  4. temperatureThen the reaction mixture was cooled to room temperature
  5. washthe mixture was washed with water and sodium bicarbonate solution
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-4c1c9279c2114946a0deb4fd51ba2639
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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