Ethylene Glycol → HCID 13175521, compound

HRID 434464Notes

Reaction equation

HRID 434464 reaction equation
[CH2:1]([O:3][CH:4]([O:26]CC)[CH2:5][N:6]([CH2:23][CH2:24][CH3:25])[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[N+:20]([O-:22])=[O:21])[CH3:2].[CH2:29](O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:44]([O:47][CH2:48][CH3:49])(=[O:46])C>C(O)C>[CH2:23]([N:6]([CH:44]1[O:47][CH2:48][CH2:49][O:46]1)[C:7]1[C:8]([N+:20]([O-:22])=[O:21])=[CH:9][C:10]([C:16]([F:17])([F:18])[F:19])=[C:11]([CH3:29])[C:12]=1[N+:13]([O-:15])=[O:14])[CH2:24][CH3:25].[CH2:23]([N:6]([CH2:5][CH:4]1[O:3][CH2:1][CH2:2][O:26]1)[C:7]1[C:8]([N+:20]([O-:22])=[O:21])=[CH:9][C:10]([C:16]([F:19])([F:17])[F:18])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 13175519HCID 13175519, compound

Product 2

HCID 13175521HCID 13175521, compoundHCID 20492555HCID 20492555, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

N-(2,2-Diethoxyethyl)-N-propyl-2,6-dinitro-4-trifluoromethylaniline (5.5 grams; 0.0132 mol), ethylene glycol (0.84 grams; 0.0132 mole), p-toluenesulfonic acid (200 mg) and ethanol solvent were placed in a glass reaction flask equipped with stirrer, heating mantle and thermometer. The mixture was heated to 120° C. After the reaction was completed, the reaction mixture was cooled to room temperature, ethyl acetate was added and the mixture was washed with water and sodium bicarbonate solution. The solution was then dried over anhydrous magnesium sulfate and evaporated to yield the desired product N-propyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline as an oil.

Workup

  1. customequipped with stirrer
  2. temperatureheating mantle
  3. temperaturethe reaction mixture was cooled to room temperature
  4. washthe mixture was washed with water and sodium bicarbonate solution
  5. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c2a5a672d5084d10a0df533b12de5e91
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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