Water → 1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole

HRID 238121ノート

反応式

HRID 238121 の反応式
[OH-].[K+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Cl.O>CS(C)=O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][N:5]1[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]1

参加物

6

反応物 4

HCID 962WaterHCID 62103,5-DimethylpyrazoleHCID 119062-Chlorobenzyl chlorideHCID 14797Potassium Hydroxide

生成物 1

HCID 6618091-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole収率 99.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
80 °C

実験手順

Powdered potassium hydroxide (1.751 g, 31.2 mmol) was added to a solution of 3,5-dimethylpyrazole (2 g, 20.81 mmol) in anhydrous DMSO (10.40 ml) and the resulting heterogeneous solution was stirred for 1.5 hr at 80° C. before being cooled to room temperature. 2-Chloro benzylchloride (2.64 ml, 20.81 mmol) was then added in 6 M DMSO over 15 min, and the solution was stirred for a further 1.5 hrs. Upon completion as observed by TLC, the reaction was poured over water and the resulting aqueous phase was extracted with two 20 mL portions of CHCl3. The combined organic layers were washed with 100 mL of water, dried with anhydrous MgSO4 and concentrated under reduced pressure to yield 4.55 g (99%) of 1-(2-chlorobenzyl)-3,5-dimethyl-1H-pyrazole as a clear liquid. 1H NMR (300 MHz, CDCl3) δ 7.41-7.31 (m, 1H), 7.24-7.09 (m, 2H), 6.59-6.50 (m, 1H), 5.90 (s, 1H), 5.31 (s, 2H), 2.26 (s, 3H), 2.15 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 148.32, 139.96, 135.46, 131.96, 129.42, 128.76, 127.72, 127.48, 105.84, 50.12, 13.80, 11.15. HRMS (m/z): [MNa]+ calc for C12H13ClN2Na+243.07. found 243.0651.

後処理

  1. temperaturebefore being cooled to room temperature
  2. stirringthe solution was stirred for a further 1.5 hrs
  3. extractionthe resulting aqueous phase was extracted with two 20 mL portions of CHCl3
  4. washThe combined organic layers were washed with 100 mL of water
  5. dry with materialdried with anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ab4372ff7d8a4d6e927411694a832348
出典データセット
uspto-grants-2014_02
特許番号
US08642614B2

反応ノート

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