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

HRID 434469Notes

Reaction equation

[CH2:1]([N:3]([CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22]CC)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18])[CH3:2].C(O)CO.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(OCC)(=O)C>[CH2:1]([N:3]([CH2:20][CH:21]1[O:22][CH2:27][CH2:26][O:25]1)[C:4]1[C:5]([N+:17]([O-:19])=[O:18])=[CH:6][C:7]([C:13]([F:14])([F:16])[F:15])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

N-Ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-4-trifluoromethylaniline (6.10 grams; 0.0154 mole), ethylene glycol (0.96 grams; 0.0154 mole) and toluenesulfonic acid (200 mg) were charged into a glass reaction vessel equipped with stirrer and thermometer. The reaction mixture was heated at 110° C. for a period of 2 hours. After this time the mixture was cooled to room temperature, dissolved in ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The washed product was then dried and stripped of solvent to yield the desired product N-ethyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-trifluoromethylaniline as an oil.

Workup

customequipped with stirrer
temperatureAfter this time the mixture was cooled to room temperature
washwashed with water and saturated aqueous sodium bicarbonate
customThe washed product was then dried

Sources & evidence

ORD record: ord-add2140de1cc4e79baf8b49895fc9e87
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04397677

Reaction notes

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