Water → 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

HRID 451005

반응식

HRID 451005 반응식
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].[OH-].[K+].O>CS(C)=O>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:4]1[CH:5]=[N:6][C:2]([CH3:1])=[N:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178433329HCID 178433329, 화합물

생성물 1

HCID 595777881-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole수율 26.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

A mixture of 3-methyl-1H-1,2,4-triazole (5.0 g, 60.2 mmol), 1-chloro-2-methoxy-4-nitrobenzene (11.3 g, 60.2 mmol), and KOH flakes (3.4 g, 48.1 mmol) in anhydrous DMSO (50 mL) was heated at 80° C. for 6 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The aqueous mixture was extracted with EtOAc (3×200 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified using silica gel chromatography (0-2% MeOH/chloroform, linear gradient) to afford 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (3.7 g, 26% yield). LC-MS (M+H)++235.2.

후처리

  1. temperatureto cool to rt
  2. extractionThe aqueous mixture was extracted with EtOAc (3×200 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified

출처 및 근거

ORD 기록
ord-280fdf67a418445fac8e5bd8a14b8590
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486952B2

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