Dimethyl Sulfoxide → 3-chloro-1-(2-methoxy-4-nitrophenyl)-1H-1,2,4-triazole

HRID 475723ノート

反応式

HRID 475723 の反応式
IC.[Cl:3][C:4]1[N:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[OH:18])[N:5]=1.[OH-].[K+].[CH3:21]S(C)=O>O>[Cl:3][C:4]1[N:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[O:18][CH3:21])[N:5]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 580752822-(3-chloro-1H-1,2,4-triazol-1-yl)-5-nitrophenol

生成物 1

HCID 580757403-chloro-1-(2-methoxy-4-nitrophenyl)-1H-1,2,4-triazole収率 65.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Iodomethane (0.860 mL, 13.82 mmol) was added to a mixture of 2-(3-chloro-1H-1,2,4-triazol-1-yl)-5-nitrophenol (1.33 g, 5.53 mmol), potassium hydroxide (0.388 g, 6.91 mmol), and DMSO (25 mL). The mixture was left to stir at rt for 24 h. The reaction mixture was poured into water (250 mL) and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified using silica gel column chromatography (0-1% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min). The pure fractions were combined and concentrated to afford 3-chloro-1-(2-methoxy-4-nitrophenyl)-1H-1,2,4-triazole (0.924 g, 3.63 mmol, 65.6% yield) as a light yellow solid. LC-MS (M+H)+=255.0. 1H NMR (500 MHz, CDCl3) δ ppm 8.35 (s, 1H) 7.36 (d, J=8.55 Hz, 1H) 6.29-6.34 (m, 2H) 3.80 (s, 3H) 2.46 (s, 3H).

後処理

  1. waitThe mixture was left
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined extracts were washed with water
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified
  9. customsilica gel column chromatography (0-1% MeOH/chloroform, linear gradient over 72 min, flow 25 mL/min)
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f1503c31dbd54f39ba8a9fa5d24aac01
出典データセット
uspto-grants-2014_01
特許番号
US08637525B2

反応ノート

読み込み中…