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

HRID 1855494ノート

反応式

HRID 1855494 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][C:14]1[N:18]=[CH:17][NH:16][N:15]=1.[OH-].[K+].Cl>CS(C)=O.O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:16]1[CH:17]=[N:18][C:14]([CH3:13])=[N:15]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178433329HCID 178433329、化合物

生成物 1

HCID 595777881-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole収率 6.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A solution of 2-chloro-5-nitroanisole (1.0 g, 5.2 mmol), 3-methyl-1H-1,2,4-triazole (1.74 g, 20.9 mmol) and potassium hydroxide (0.44 g, 7.8 mmol) in dimethyl sulfoxide (5 ML) was heated to 80° C. under an atmosphere of nitrogen for two days. Water and 1M aqueous hydrogen chloride solution was added and the reaction was stirred for 45 minutes. The precipitate was filtered off, washed with water, dissolved in dichloromethane. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound as a yellow solid (77 mg, 6%). MS ISP (m/e): 235.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.88 (s, 1H), 8.10 (d, 1H), 7.96-8.02 (m, 2H), 4.10 (s, 3H), 2.51 (s, 3H).

後処理

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. dissolutiondissolved in dichloromethane
  4. extractionThe aqueous layer was extracted twice with dichloromethane
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by reversed preparative HPLC

出典と根拠

ORDレコード
ord-050c11c351594566a97003c5fe09da5b
出典データセット
uspto-grants-2015_02
特許番号
US08962834B2

反応ノート

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