Ethylene Glycol → N-methyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline

HRID 434466Notes

Reaction equation

[CH3:1][N:2]([CH2:19][CH:20]([O:23][CH3:24])[O:21][CH3:22])[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17].C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[CH3:1][N:2]([CH2:19][CH:20]1[O:23][CH2:24][CH2:22][O:21]1)[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([C:12]([F:14])([F:15])[F:13])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17]

Participants

Conditions

Temperature: 120 °C

Procedure

N-Methyl-N-(2,2-dimethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline (3.2 grams; 0.0915 mole), ethylene glycol 0.57 grams; 0.0915 mole), para-toluenesulfonic acid (200 mg) and ethyl acetate were charged into a glass reaction vessel equipped with a stirrer, heating mantle, reflux condenser and thermometer. The reaction mixture was heated at 120° C. with stirring for one hour. After this time the mixture was cooled to room temperature and washed with aqueous sodium bicarbonate. The washed solution was dried over anhydrous sodium sulfate, filtered and stripped of solvent leaving a solid residue. The residue was recrystallized from hexane to yield the desired N-methyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline as a yellow crystalline solid melting at 83° C.

Workup

customequipped with a stirrer
temperatureheating mantle
temperaturereflux condenser
temperatureAfter this time the mixture was cooled to room temperature
washwashed with aqueous sodium bicarbonate
dry with materialThe washed solution was dried over anhydrous sodium sulfate
filtrationfiltered
customleaving a solid residue
customThe residue was recrystallized from hexane

Sources & evidence

ORD record: ord-d044922c19884a479fe10b02493d758f
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04397677

Reaction notes

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