Ammonia → Prodiamine

HRID 2071241Notes

Reaction equation

HRID 2071241 reaction equation
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[C:7](Cl)[C:6]=1[N+:19]([O-:21])=[O:20])[CH2:2][CH3:3].[NH3:25]>C(O)C>[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[C:5]1[C:6]([N+:19]([O-:21])=[O:20])=[C:7]([NH2:25])[C:8]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 94399Benzenamine, 3-chloro-2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)-

Product 1

HCID 34469Prodiamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A glass reaction tube was charged with 4.0 grams (0.0108 mole) of N,N-di-n-propyl-3-chloro-2,6-dinitro-4-trifluoromethylaniline, 5.82 grams (0.0237 mole) of 6.95% ethanolic ammonia and 35 ml. of ethanol. The tube was sealed and heated in an oven at 100° C. for 68 hours. The contents of the tube were cooled and the ethanol removed by evaporation. Water was added to the solid orange residue to dissolve the ammonium chloride and the insoluble produced was separated by filtration. The product was dissolved in refluxing 95% ethanol. Upon cooling, orange needles and a yellow powder crystallized. The yellow powder was identified as 2,4-dinitro-6-trifluoromethyl-1,3-phenylenediamine and was separated from the desired product by filtration after extracting with boiling hexane. The desired product dissolved in the hexane and was isolated from the filtrate by evaporation of the hexane. The residue was recrystallized from 95% ethanol to give orange needles, m.p. 124°-125° C.

Workup

  1. customA glass reaction tube
  2. customThe tube was sealed
  3. temperatureThe contents of the tube were cooled
  4. customthe ethanol removed by evaporation
  5. additionWater was added to the solid orange residue
  6. dissolutionto dissolve the ammonium chloride
  7. customthe insoluble produced
  8. customwas separated by filtration
  9. dissolutionThe product was dissolved
  10. temperaturein refluxing 95% ethanol
  11. temperatureUpon cooling
  12. customorange needles and a yellow powder crystallized
  13. customwas separated from the desired product by filtration
  14. extractionafter extracting with boiling hexane
  15. dissolutionThe desired product dissolved in the hexane
  16. customwas isolated from the filtrate by evaporation of the hexane
  17. customThe residue was recrystallized from 95% ethanol
  18. customto give orange needles, m.p. 124°-125° C.

Sources & evidence

ORD record
ord-e59f9dfbcc2f4b3aa917c89a9f03d7ce
Source dataset
uspto-grants-1977_09
Patent number
US04046758

Reaction notes

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