Phenylisocyanide → 5-iodo-1-phenyltetrazole

HRID 553754Notes

Reaction equation

HRID 553754 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[I:5]N1C(=O)CCC1=O.[C:13]1([N+:19]#[C-:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.[I-].C[N+](C)(C)C.C(Cl)(Cl)Cl>[I:5][C:20]1[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=[N:2][N:1]=1

Participants

7

Reactant 3

HCID 13606PhenylisocyanideHCID 33557Sodium AzideHCID 120273N-Iodosuccinimide

Product 1

HCID 9145025-iodo-1-phenyltetrazole

Reagents, catalysts & solvents 3

HCID 638175-58-1CatalystHCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

With vigorous stirring, a solution of 9.7 mmol (0.63 g) of sodium azide in 10 ml of water and 0.1 g of tetramethylammonium iodide are added to a mixture, cooled to 0° C., of 9.7 mmol (2.18 g) of N-iodosuccinimide in 10 ml of chloroform. After 5 minutes of stirring, a solution of 9.7 mmol (1 g) of phenyl isocyanide in chloroform is added dropwise, and the reaction mixture is stirred at 0° C. for 45 minutes. The reaction mixture is allowed to warm to room temperature, and a further 10 ml of chloroform are added. The phases are separated, and the organic phase is washed 3 times with water, once with saturated sodium thiosulfate solution, again with water and then with saturated sodium chloride solution. After drying over sodium sulfate, the solvent is distilled off under reduced pressure and the residue is recrystallized from ethanol or petroleum (bp.: 80 . . . 110° C.)/ethyl acetate. This gives 0.2 g (8%) of 5-iodo-1-phenyltetrazole of melting point 123-129° C.

Workup

  1. stirringthe reaction mixture is stirred at 0° C. for 45 minutes
  2. customThe phases are separated
  3. washthe organic phase is washed 3 times with water
  4. dry with materialAfter drying over sodium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is recrystallized from ethanol or petroleum (bp.: 80 . . . 110° C.)/ethyl acetate

Sources & evidence

ORD record
ord-ab939f93a7bd46d1aa5820012aaf2da9
Source dataset
uspto-grants-2011_11
Patent number
US08048903B2

Reaction notes

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