Allyl bromide → N-Allyl-2,6-dinitro-4-ethyl-N-methoxyaniline

HRID 371692Notes

Reaction equation

HRID 371692 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=[C:11]([N+:17]([O-:19])=[O:18])[C:7]=1[NH:8][O:9][CH3:10])([O-:5])=[O:4].[CH2:20](Br)[CH:21]=[CH2:22]>CN(C)C=O>[CH2:22]([N:8]([O:9][CH3:10])[C:7]1[C:6]([N+:3]([O-:5])=[O:4])=[CH:14][C:13]([CH2:15][CH3:16])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 213298884-Ethyl-N-methoxy-2,6-dinitroaniline

Product 1

HCID 21329876N-Allyl-2,6-dinitro-4-ethyl-N-methoxyanilineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.017 mole of sodium hydride, obtained from 0.82 g. of a 50% dispersion of sodium hydride in mineral oil (by the process described in Example 11, supra), was added 50 ml. of dimethylformamide. To the suspension was added 3.0 g. (0.012 mole) of 2,6-dinitro-4-ethyl-N-methoxyaniline (Example 2), and the mixture stirred for about 5-10 minutes. Allyl bromide, 2.9 g. (0.024 mole), was added and the reaction mixture stirred at room temperature for about 30 minutes. A sample of the reaction mixture checked by NMR showed the presence of about 70-80 percent of the desired product, together with about 20-30 percent of starting material. The reaction mixture was then heated at about 90° C., with stirring, for about an hour. A check by NMR indicated the reaction had gone to completion. The reaction product mixture was worked up by adding dilute aqueous hydrochloric acid and toluene. The organic layer was separated and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was chromatographed on a Florisil column. The fractions were examined by NMR spectrum, combined, and concentrated in vacuo to dryness. The residue was recrystallized from petroleum ether (b.p. 60°-71° C.) to give 1.7 g. of product having a melting point of about 83°-85° C. The product was identified by NMR spectrum and elemental analyses as N-allyl-2,6-dinitro-4-ethyl-N-methoxyaniline.

Workup

  1. additionwas added 50 ml
  2. additionTo the suspension was added 3.0 g
  3. addition(0.024 mole), was added

Sources & evidence

ORD record
ord-68c2217ba0e94a6f8579c3c972812676
Source dataset
uspto-grants-1978_05
Patent number
US04087460

Reaction notes

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