Hydrochloric Acid → N~1~-(4-Azido-2-nitrophenyl)propane-1,3-diamine

HRID 638528Notes

Reaction equation

HRID 638528 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH2:5].F[C:7]1[CH:12]=[CH:11][C:10]([N:13]=[N+:14]=[N-:15])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17].O.Cl>C(O)C>[N:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:1][CH2:2][CH2:3][CH2:4][NH2:5])=[C:8]([N+:16]([O-:18])=[O:17])[CH:9]=1)=[N+:14]=[N-:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4281,3-PropanediamineHCID 962WaterHCID 931211-Fluoro-2-nitro-4-azidobenzene

Product 1

HCID 12716508N~1~-(4-Azido-2-nitrophenyl)propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.5 ml (30 mM) 1,3-diaminopropane was dissolved in 25 ml ethanol. To this solution, was added a solution of 1.82 g (10 mM) 4-fluoro-3-nitrophenyl azide in 25 ml ethanol. The addition was performed dropwise with stirring. The mixture was stirred at room temperature for 16 hours. After this time, 150 ml of water were added and the pH adjusted to between 1 and 2 with concentrated HCl. This solution was filtered to remove the disubstituted amine, cooled on ice and the product was precipitated by the slow addition of concentrated aqueous ammonia with stirring. The product was collected by filtration of the cold mixture, washed with ice-cold water and dried in vacuo.

Workup

  1. additionThe addition
  2. stirringThe mixture was stirred at room temperature for 16 hours
  3. filtrationThis solution was filtered
  4. customto remove the disubstituted amine
  5. temperaturecooled on ice
  6. customthe product was precipitated by the slow addition of concentrated aqueous ammonia
  7. stirringwith stirring
  8. filtrationThe product was collected by filtration of the cold mixture
  9. washwashed with ice-cold water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-084583ee2b79404bb86e4065d52346e4
Source dataset
uspto-grants-1985_12
Patent number
US04562157

Reaction notes

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