Isocyanobenzene → 5-iodo-1-phenyltetrazole

HRID 553754노트

반응식

HRID 553754 반응식
[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

참가 물질

7

반응물 3

HCID 13606IsocyanobenzeneHCID 33557Sodium AzideHCID 120273N-Iodosuccinimide

생성물 1

HCID 9145025-iodo-1-phenyltetrazole

시약·촉매·용매 3

HCID 6381Tetramethylammonium iodide촉매HCID 962Water용매HCID 6212Chloroform용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab939f93a7bd46d1aa5820012aaf2da9
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048903B2

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