Sec-Butylamine → 3-Chloro-N-(1-methylpropyl)-2,4-dinitro-6-(trifluoromethyl)benzenamine

HRID 2071234Notes

Reaction equation

HRID 2071234 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20]>C(O)C>[CH:19]([NH:23][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([Cl:11])[C:7]=1[N+:8]([O-:10])=[O:9])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 214130983-Chloro-N-(1-methylpropyl)-2,4-dinitro-6-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 20 g. (0.0655 mole) of 2,4-dichloro-3,5-dinitrobenzotrifluoride and 150 ml. of absolute ethanol was added 9.58 g. (0.131 mole) of sec-butylamine, dropwise, over a period of about 15 minutes. The resultant solution was refluxed for 2 hours and the ethanol then removed by distillation under reduced pressure. The solid yellow residue was triturated with 300 ml. water to dissolve the sec-butylamine hydrochloride. The water insoluble product was isolated by filtration, washed with water, and then dissolved in 600 ml. of refluxing 95% ethanol. Upon cooling, the product crystallized. Filtration gave 20.4 g. of a yellow crystalline solid, melting at 90.5°-91.5° C.

Workup

  1. additionTo a stirred mixture of 20 g
  2. customthe ethanol then removed by distillation under reduced pressure
  3. customThe solid yellow residue was triturated with 300 ml
  4. dissolutionwater to dissolve the sec-butylamine hydrochloride
  5. customThe water insoluble product was isolated by filtration
  6. washwashed with water
  7. dissolutiondissolved in 600 ml
  8. temperatureof refluxing 95% ethanol
  9. temperatureUpon cooling
  10. customthe product crystallized
  11. filtrationFiltration
  12. customgave 20.4 g

Sources & evidence

ORD record
ord-49d959a8607f439c9c246ef9640b1ad1
Source dataset
uspto-grants-1977_09
Patent number
US04046758

Reaction notes

Loading…