Isocyanobenzene → 5-iodo-1-phenyltetrazole

HRID 553754ノート

反応式

HRID 553754 の反応式
[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

参加物

7

反応物 3

HCID 13606IsocyanobenzeneHCID 33557Sodium AzideHCID 120273N-Iodosuccinimide

生成物 1

HCID 9145025-iodo-1-phenyltetrazole

試薬・触媒・溶媒 3

HCID 6381Tetramethylammonium iodide触媒HCID 962Water溶媒HCID 6212Chloroform溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab939f93a7bd46d1aa5820012aaf2da9
出典データセット
uspto-grants-2011_11
特許番号
US08048903B2

反応ノート

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