Hexamethylenediamine → 2-Chloro-3-phenoxy-6-nitro-N-(6-amino-hexyl)-aniline

HRID 1902600Notes

Reaction equation

HRID 1902600 reaction equation
[Cl:1][C:2]1[C:7](OC2C=CC=CC=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32]>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH2:32]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 128811472-Chloro-4-nitro-1,3-diphenoxy-benzene

Product 1

HCID 205145282-Chloro-3-phenoxy-6-nitro-N-(6-amino-hexyl)-aniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 17.5 gm of 2-chloro-4-nitro-1,3-diphenoxy-benzene, 30 ml of dioxane and 9 gm of 1,6-diaminohexane was stirred for 4 hours at 50° C. Thereafter, the dioxane was distilled off, the residue was taken up in chloroform, the resulting solution was washed first with dilute sodium hydroxide and then with dilute hydrochloric acid, dried with sodium sulfate, and the chloroform was distilled off. The residue was dissolved in diethyl ether, gaseous hydrogen chloride was passed through the resulting solution, the precipitate formed thereby was collected by suction filtration, and the semi-solid filter cake was stirred with a mixture of chloroform and an aqueous sodium carbonate solution. The organic phase was separated, dried with sodium sulfate, and the chloroform was distilled off, leaving 12.5 gm (69% of theory) of the title compound as a viscous yellow oil.

Workup

  1. distillationThereafter, the dioxane was distilled off
  2. washthe resulting solution was washed first with dilute sodium hydroxide
  3. dry with materialwith dilute hydrochloric acid, dried with sodium sulfate
  4. distillationthe chloroform was distilled off
  5. dissolutionThe residue was dissolved in diethyl ether
  6. customthe precipitate formed
  7. filtrationthereby was collected by suction filtration
  8. filtrationthe semi-solid filter cake
  9. stirringwas stirred with a mixture of chloroform
  10. customThe organic phase was separated
  11. dry with materialdried with sodium sulfate
  12. distillationthe chloroform was distilled off

Sources & evidence

ORD record
ord-c4bba2f3885149e4be20195f2757905e
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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