Ethanol → Benzenamine, N-methoxy-2,6-dinitro-4-(trifluoromethyl)-

HRID 614035Notes

Reaction equation

HRID 614035 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].C(O)C.C(N(CC)CC)C.Cl.[CH3:29][O:30][NH2:31]>C(OCC)(=O)C>[N+:15]([C:3]1[CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:31][O:30][CH3:29])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 521874O-Methylhydroxylamine hydrochloride2×

Product 1

HCID 12102672Benzenamine, N-methoxy-2,6-dinitro-4-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution prepared from 27.0 g. (0.1 mole) of 4-chloro-3,5-dinitrobenzotrifluoride in 200 ml. of ethanol there was added 25.25 g. (0.25 mole) of triethylamine, and 12.5 g. (0.15 mole) of methoxyamine hydrochloride. Upon the addition of the methoxyamine hydrochloride, the temperature of the reaction mixture rose to about 50° C. The reaction mixture was allowed to stir for about 1.5 hours and the reaction product mixture was worked up by diluting it with ethyl acetate, washing several times with dilute hydrochloric acid and water, and drying the organic layer over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate concentrated on the steam bath to leave a residue. The residue was allowed to chill over the weekend in the refrigerator and crystals separated. The crystalline product was filtered off. It had a melting point of about 135°-137° C., weighed 21.0 g., and was identified by NMR spectrum and elemental analyses as 2,6-dinitro-N-methoxy-α,α,α-trifluoro-p-toluidine.

Workup

  1. customTo a solution prepared from 27.0 g
  2. customrose to about 50° C
  3. washwashing several times with dilute hydrochloric acid and water
  4. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate concentrated on the steam bath
  7. customto leave a residue
  8. temperatureto chill over the weekend in the refrigerator and crystals
  9. customseparated
  10. filtrationThe crystalline product was filtered off

Sources & evidence

ORD record
ord-0ab82760d01f4cd4a91023f21ae96ebe
Source dataset
uspto-grants-1979_03
Patent number
US04143073

Reaction notes

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