Hydrochloric Acid → HCID 67359403, compound

HRID 1916044Notes

Reaction equation

HRID 1916044 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[N:9][O:10][C:6]=2[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][N:3]=1.C([NH:21][CH2:22][CH2:23][CH2:24][NH2:25])(OC(C)(C)C)=O.Cl>CO.O1CCOCC1>[N+:11]([C:5]1[C:6]2[O:10][N:9]=[CH:8][C:7]=2[C:2]([NH:21][CH2:22][CH2:23][CH2:24][NH2:25])=[N:3][CH:4]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 22677215HCID 22677215, compound

Product 1

HCID 67359403HCID 67359403, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-7-nitro-[1,2,5]benzoxadiazole (100 mg, 0.501 mmol) was dissolved in methanol (5 ml). N-Boc-1,3-propanediamine (44 mg, 0.25 mmol) was then added and the reaction mixture stirred overnight. The solvent was evaporated and the residue was purified using silica gel chromatography with ethyl acetate:hexane (1:1) to afford dark brown solid. This material was then treated with a solution of 4.0 M HCl in dioxane (excess) overnight to remove the Boc group. The solution was evaporated to afford N1-(7-nitro-[1,2,5]benzoxadiazol-4-yl)propane-1,3-diamine as the hydrochloride salt, which was used without further purification. Yield: 60 mg (51%). MS (m/z): (M+H)=237.22.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified
  3. customto afford dark brown solid
  4. customto remove the Boc group
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-96728120a60a47a7b02cb25581e77fe3
Source dataset
uspto-grants-2013_12
Patent number
US08618096B2

Reaction notes

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