1H-1,2,4-Triazole → 3,5-Diethoxy-4-[1,2,4]triazol-1-yl-benzaldehyde

HRID 502421ノート

反応式

HRID 502421 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH2:14][CH3:15])[C:11]=1F)[CH:7]=[O:8])[CH3:2].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:13][CH2:14][CH3:15])[C:11]=1[N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH:7]=[O:8])[CH3:2]

参加物

5

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 591282733,5-Diethoxy-4-fluoro-benzaldehyde

生成物 1

HCID 587063313,5-Diethoxy-4-[1,2,4]triazol-1-yl-benzaldehyde収率 85.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

5.00 g (23.6 mMol) of 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), 3.25 g (=2.0 eq.) of 1,2,4-triazole and 6.51 g (=2.0 eq.) of potassium carbonate was dissolved under argon in 50 mL of DMSO; the reaction mixture was stirred for 1 hour at 110° C. Then, it was cooled down to ambient temperature, poured into crashed ice and extracted twice with ethyl acetate. The organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of n-heptane/ethyl acetate) to yield 5.28 g of the title compound as colorless solid. MS: 261.9 (MH+).

後処理

  1. temperatureThen, it was cooled down to ambient temperature
  2. additionpoured
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phases were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated i.V
  8. customThe crude product was purified by chromatography (silicagel, eluent:gradient of n-heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-0f25d7d5e1b64cccb9ce6e8aadd3468f
出典データセット
uspto-grants-2010_08
特許番号
US07772253B2

反応ノート

読み込み中…