Iodine → HCID 11608517, compound

HRID 553753Notes

Reaction equation

HRID 553753 reaction equation
C([Li])CCC.[CH2:6]([N:10]1[CH:14]=[N:13][N:12]=[N:11]1)[CH2:7][CH2:8][CH3:9].[I:15]I.O>O1CCCC1>[I:15][C:14]1[N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[N:11]=[N:12][N:13]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 121443861H-Tetrazole, 1-butyl-HCID 178418339Butyllithium

Product 1

HCID 11608517HCID 11608517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

In an atmosphere of inert gas, 0.032 mol (20 ml) of butyllithium (1.6M in hexane) is added dropwise to a solution, cooled to −78° C., of 0.03 mol (3.78 g) of 1-butyltetrazole in 40 ml of anhydrous tetrahydrofuran such that the temperature of the reaction mixture does not exceed −70° C. The mixture is stirred at this temperature for 30 minutes, and 0.03 mol (7.61 g) of iodine in 10 ml of anhydrous tetrahydrofuran is then added dropwise. After 30 minutes of stirring at this temperature, the reaction mixture is warmed to −30° C., and 1 ml of water is added carefully. The solvent is distilled off under reduced pressure and the residue is taken up in ethyl acetate/water. The aqueous phase is extracted with ethyl acetate and the combined organic phase is washed with sodium thiosulfate solution and saturated sodium chloride solution and dried over sodium sulfate. The residue obtained after distillative removal of solvent under reduced pressure is purified chromatographically (mobile phase: chloroform). This gives 2.2 g (30%) of 5-iodo-1-butyltetrazole

Workup

  1. customdoes not exceed −70° C
  2. stirringAfter 30 minutes of stirring at this temperature
  3. distillationThe solvent is distilled off under reduced pressure
  4. extractionThe aqueous phase is extracted with ethyl acetate
  5. washthe combined organic phase is washed with sodium thiosulfate solution and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe residue obtained
  8. customafter distillative removal of solvent under reduced pressure
  9. customis purified chromatographically (mobile phase: chloroform)

Sources & evidence

ORD record
ord-b69e166643434a50b23f7d428de7bcc6
Source dataset
uspto-grants-2011_11
Patent number
US08048903B2

Reaction notes

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