Dimethylamine → 4-tert-Butyl-N,N-dimethyl-2,6-dinitroaniline

HRID 1678834Notes

Reaction equation

HRID 1678834 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][NH:19][CH3:20].C(O)C>O>[CH3:18][N:19]([CH3:20])[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 674DimethylamineHCID 702EthanolHCID 751764-tert-Butyl-2,6-dinitrochlorobenzene

Product 1

HCID 203642434-tert-Butyl-N,N-dimethyl-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 dimethylamine in 50 ml. ethanol. The temperature was slowly increased as follows: 30° C. for 1 hour, 40° C. for 1 hour, 50° C. for one hour, then 80° C. for five 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,N-dimethyl-2,6-dinitro-4-t-butylaniline in the form of orange-yellow needles melting at 101-102° C.

Workup

  1. temperatureThe temperature was slowly increased
  2. wait40° C. for 1 hour
  3. wait50° C. for one hour
  4. wait80° C. for five 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-3e70a35179374916b3a01ab5979ed78b
Source dataset
uspto-grants-1978_03
Patent number
US04077795

Reaction notes

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