Triethylamine → 5-benzyl-1-phenyl-1H-1,2,4-triazole

HRID 2232971ノート

反応式

HRID 2232971 の反応式
Cl.[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:17]([NH:19][C:20](=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O>C(O)(=O)C>[CH2:21]([C:20]1[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[CH:17][N:19]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 60962Phenylhydrazine hydrochlorideHCID 3268658N-formyl-2-phenylacetamide

生成物 1

HCID 107284635-benzyl-1-phenyl-1H-1,2,4-triazole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

Phenylhydrazine hydrochloride (0.09 g, 0.6 mmol) in 5 mL glacial acetic acid was treated with triethylamine (0.06 g, 0.6 mmol), warmed to 70° C., treated with N-formylphenylacetamide (0.1 g, 0.6 mmol), and heated at 90° C. for 1 hour. The mixture was then allowed to cool to room temperature and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the organics were washed with saturated NaHCO3, 1M NaOH, water, and brine. The organics were then dried (MgSO4), and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (40% hexanes/ethyl acetate) to provide the title compound. MS (ESI) m/e: 236 (M+H)+; 1H NMR (DMSO-d6) δ 4.2 (s, 2H), 7.05-7.1 (d, 2H), 7.17-7.3 (m, 3H), 7.45-7.6 (m, 5H), 8.1 (s, 1H); Anal. calcd. for C, 76.57; H, 5.57; N, 17.86. Found C, 76.32; H: 5.81; N, 17.63.

後処理

  1. temperatureheated at 90° C. for 1 hour
  2. temperatureto cool to room temperature
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organics were washed with saturated NaHCO3, 1M NaOH, water, and brine
  6. dry with materialThe organics were then dried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (40% hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-e36d3b951f094df9bf03d634389e1497
出典データセット
uspto-grants-2010_05
特許番号
US07709469B2

反応ノート

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