Hydrochloric Acid → 5-(4-fluorobenzyl)-2H-tetrazole

HRID 2099587ノート

反応式

HRID 2099587 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:11]=[N:12][NH:13][N:10]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 33557Sodium AzideHCID 68016Benzeneacetonitrile, 4-fluoro-

生成物 1

HCID 106074055-(4-fluorobenzyl)-2H-tetrazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a solution of (4-fluorophenyl)acetonitrile (5.00 g, 37.0 mmol) in 100 mL of toluene was added sodium azide (7.22 g, 111 mmol), triethylamine (15.5 mL, 111 mmol), and concentrated aqueous HCl solution (9.25 mL, 111 mmol). The reaction was heated at 90° C. overnight. The solution was cooled to room temperature and extracted with water and 1N NaOH solution. The combined aqueous layers were washed with ether (3×), acidified with concentrated aqueous HCl solution, and the resulting precipitate was collected by filtration and rinsed with 0.1N HCL solution. The resulting solid was azeotroped from toluene to provide 5-(4-fluorobenzyl)-2H-tetrazole. ESI+MS: 178.9 [M+H]+.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with water and 1N NaOH solution
  3. washThe combined aqueous layers were washed with ether (3×)
  4. filtrationthe resulting precipitate was collected by filtration
  5. washrinsed with 0.1N HCL solution
  6. customThe resulting solid was azeotroped from toluene

出典と根拠

ORDレコード
ord-8d2a129ce5d34b87bbe44383b13606ab
出典データセット
uspto-grants-2009_08
特許番号
US07569589B2

反応ノート

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