Cyanoacetic acid hydrazide → 2-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)acetonitrile

HRID 1397319ノート

反応式

HRID 1397319 の反応式
[C:1]([CH2:3][C:4]([NH:6][NH2:7])=O)#[N:2].[OH-].[Na+].Cl.[F:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[NH:19])OC)=[CH:14][CH:13]=1>CO.CCOC(C)=O>[F:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]2[N:19]=[C:4]([CH2:3][C:1]#[N:2])[NH:6][N:7]=2)=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 8820Cyanoacetic acid hydrazideHCID 14798Sodium HydroxideHCID 14685563Methyl 4-fluorobenzimidate hydrochloride

生成物 1

HCID 508774582-(3-(4-Fluorophenyl)-1H-1,2,4-triazol-5-yl)acetonitrile収率 47%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Cyanoacetohydrazide (172 mg, 1.74 mmol) and NaOH (66 mg, 1.66 mmol) were added to a solution of methyl 4-fluorobenzimidate hydrochloride (300 mg, 1.58 mmol) in dry MeOH (5 mL) and the mixture was heated to reflux for 1 h. The reaction mixture was concentrated under reduced pressure and the residue obtained was diluted with EtOAc. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 20-25% EtOAc in petroleum ether) to yield 2-(3-(4-fluorophenyl)-1H-1,2,4-triazol-5-yl)acetonitrile (150 mg, yield 47%). 1H NMR (400 MHz, DMSO-d6) δ 8.04-7.99 (m, 2H), 7.39-7.33 (m, 2H), 4.11 (s, 2H). MS (ESI) m/z: Calculated for C10H7FN4: 202.07. found: 203.2 (M+H)+.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue obtained
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 20-25% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-9967a86419b043829dff89a5869a7e1a
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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