Sec-Butylamine → N-sec-Butyl-3,4-dimethyl-2,6-dinitroaniline

HRID 1833280Notes

Reaction equation

HRID 1833280 reaction equation
Cl[C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH3:12])[C:5]([CH3:11])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:16]([NH2:20])([CH2:18][CH3:19])[CH3:17]>C1(C)C(C)=CC=CC=1>[CH:16]([NH:20][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[C:4]([CH3:12])[C:3]=1[N+:13]([O-:15])=[O:14])([CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 134551024-Chloro-3,5-dinitro-o-xylene

Product 1

HCID 12767672N-sec-Butyl-3,4-dimethyl-2,6-dinitroaniline

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4-chloro-3,5-dinitro-o-xylene (140 grams, 0.61 mole), mono-sec-butylamine (184 ml., 1.82 moles), and xylene (1400 ml.) is brought to reflux. After refluxing overnight, the reaction mixture is cooled and filtered. The precipitate is washed with petroleum ether. The filtrate and washings are combined, washed with 500 ml. of 10% hydrochloric acid, and finally with 2 liters of water. The organic layer is separated and dried. Removal of the drying agent and the solvent leaves an orange oil which crystallizes with the addition of petroleum ether. A yellow orange solid (150.6 grams, 86.5%) with melting point 42° C. to 43° C. is collected.

Workup

  1. temperatureto reflux
  2. temperatureAfter refluxing overnight
  3. temperaturethe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe precipitate is washed with petroleum ether
  6. washwashed with 500 ml
  7. customThe organic layer is separated
  8. customdried
  9. customRemoval of the drying agent
  10. customthe solvent leaves an orange oil which
  11. customcrystallizes with the addition of petroleum ether
  12. customA yellow orange solid (150.6 grams, 86.5%) with melting point 42° C. to 43° C. is collected

Sources & evidence

ORD record
ord-f76c4764150b40eb9e5c608f8d698fef
Source dataset
uspto-grants-1978_01
Patent number
US04066441

Reaction notes

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