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

HRID 2232971노트

반응식

HRID 2232971 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e36d3b951f094df9bf03d634389e1497
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709469B2

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