Toluene → N-ethyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-4-t-butylaniline

HRID 434472Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](Cl)=[C:7]([N+:15]([O-:17])=[O:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:18]1[CH2:22][CH2:21][O:20][CH:19]1[CH2:23][NH:24][CH2:25][CH3:26].C1(C)C=CC=CC=1>C(OCC)C>[CH2:25]([N:24]([CH2:23][CH:19]1[O:20][CH2:21][CH2:22][O:18]1)[C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[CH3:26]

Participants

Conditions

Temperature: 90 °C

Procedure

4-t-Butyl-2,6-dinitrochlorobenzene (1.8 grams; 0.007 mole), N-(1,3-dioxolan-2-yl)methyl ethylamine (1.83 grams; 0.014 mole) and toluene (50 ml) were placed in a glass reaction vessel equipped with a stirrer, heating mantle, reflux condenser and thermometer. The reaction mixture was heated to 90° C. and maintained at this temperature with stirring for 72 hours. Diethyl ether (50 ml) was added to the cooled reaction mixture, which was filtered and evaporated to a volume of 10 cc. The residue was chromatographed on silica to remove unreacted starting material. The product (1.7 grams) was obtained as an oil which solidified on standing (73°-74° C. melting point). The product was analyzed for C16H23N3O6 :

Workup

customequipped with a stirrer
temperatureheating mantle
temperaturereflux condenser
temperaturemaintained at this temperature
filtrationwas filtered
customevaporated to a volume of 10 cc
customThe residue was chromatographed on silica
customto remove unreacted

Sources & evidence

ORD record: ord-5abeee687b1447eb9f0e62129eace042
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04397677

Reaction notes

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