Ethylene Glycol → N-ethyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-p-toluidine

HRID 434471Notes

Reaction equation

HRID 434471 reaction equation
[CH2:1]([N:3]([CH2:17][CH:18]([O:22][CH2:23]C)[O:19][CH2:20]C)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([CH3:13])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15])[CH3:2].C(O)CO.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(OCC)(=O)C>[CH2:1]([N:3]([CH2:17][CH:18]1[O:19][CH2:20][CH2:23][O:22]1)[C:4]1[C:5]([N+:14]([O-:16])=[O:15])=[CH:6][C:7]([CH3:13])=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 69252-Methylbenzenesulfonic acidHCID 20492554N-(2,2-Diethoxyethyl)-N-ethyl-4-methyl-2,6-dinitroaniline

Product 1

HCID 20492556N-ethyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-p-toluidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

N-Ethyl-N-(2,2-diethoxyethyl)-2,6-dinitro-p-toluidine (5.2 grams; 0.0132 mole), ethylene glycol (0.82 grams; 0.0132 mole) and toluenesulfonic acid (200 mg) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was heated at 110° C. for a period of one hour. After this time the mixture was dissolved in ethyl acetate and the resulting solution washed with aqueous base, dried and stripped of solvent to yield the desired product N-ethyl-N-1,3-dioxolan-2-ylmethyl-2,6-dinitro-p-toluidine as a brown oil.

Workup

  1. customequipped with a mechanical stirrer
  2. washthe resulting solution washed with aqueous base
  3. customdried

Sources & evidence

ORD record
ord-5868251266d543e2b3ff22f2a99f7619
Source dataset
uspto-grants-1983_08
Patent number
US04397677

Reaction notes

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