Ethanol → 4-tert-Butyl-N-methyl-2,6-dinitroaniline

HRID 1730110Notes

Reaction equation

HRID 1730110 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([N+:14]([O-:16])=[O:15])[C:5]=1Cl)([O-:3])=[O:2].[CH3:18][NH2:19].C(O)C>O>[CH3:18][NH:19][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 751764-tert-Butyl-2,6-dinitrochlorobenzene

Product 1

HCID 6172794-tert-Butyl-N-methyl-2,6-dinitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Two and six-tenths grams (.01 mole) of 2,6-dinitro-4-t-butylchlorobenzene was reacted with 3.1 grams of 40% aqueous solution of methylamine in 50 ml. ethanol. The temperature was slowly increased as follows: 30° C for 1 hour; 40° C for 1 hour; 50° C for 1 hour, then 80° C for 5 hours. When the reaction was complete about 100 ml. H2O was added, precipitating the product. This was filtered, washed with portions of H2O and upon recrystallization from ethanol yielded 2.5 grams of N-methyl-2,6-dinitro-4-t-butylaniline as orange needles melting at 129°-130° C.

Workup

  1. temperatureThe temperature was slowly increased
  2. wait40° C for 1 hour
  3. wait50° C for 1 hour
  4. wait80° C for 5 hours
  5. customprecipitating the product
  6. filtrationThis was filtered
  7. washwashed with portions of H2O and upon recrystallization from ethanol

Sources & evidence

ORD record
ord-627193cdab8849c883b570d0ef158060
Source dataset
uspto-grants-1976_11
Patent number
US03991116

Reaction notes

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