1,4-Diazidobutane → HCID 178420369, compound

HRID 2393722Notes

Reaction equation

HRID 2393722 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][N:8]=[N+:9]=[N-:10])=[N+:2]=[N-:3].[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([NH:3][N:2]=[N:1][CH2:4][CH2:5][CH2:6][CH2:7][N:8]=[N:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 136209641,4-DiazidobutaneHCID 178418336HCID 178418336, compound

Product 1

HCID 178420369HCID 178420369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.40 g (10 mmoles) of 1,4-diazidobutane, in 10 ml. of THF and chilled to -45° C., was treated dropwise with 15 ml of 2.0M benzylmagnesium chloride in THF (30 mmoles). The reaction mixture was magnetically stirred overnight at room temperature. The solvent was removed under vacuum and the residue was dissolved in 200 ml. of diethylether and washed with 30 ml. of ammonium buffer (50 g. ammonium chloride, 178 ml. of 10% ammonium hydroxide and 272 ml. of water), followed by 2×30 ml of water. The solution was dried over sodium sulfate and concentrated on a rotary evaporator and dried under high vacuum at room temperature. The crude product was recrystallized from diethylether in the -20° freezer to produce 2.6 g. of white crystals m.p. 71°-74° C. The nmr and mass spectra were fully consistent with the structure.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in 200 ml
  3. washof diethylether and washed with 30 ml
  4. dry with materialThe solution was dried over sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customdried under high vacuum at room temperature
  7. customThe crude product was recrystallized from diethylether in the -20° freezer
  8. customto produce 2.6 g

Sources & evidence

ORD record
ord-337e11d4d1b04d46af92df0b7ef1cb2c
Source dataset
uspto-grants-1998_09
Patent number
US05808038

Reaction notes

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