2-Iodobutane → 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole

HRID 2359082ノート

反応式

HRID 2359082 の反応式
[I:1][C:2]1[C:3]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:4][NH:5][CH:6]=1.[H-].[Na+].I[CH:15]([CH2:17][CH3:18])[CH3:16].C(N1C=C(I)C(C2SC=CC=2)=N1)(CC)C>CN(C)C=O.CC(OC)(C)C.O>[CH:15]([N:4]1[C:3]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[C:2]([I:1])[CH:6]=[N:5]1)([CH2:17][CH3:18])[CH3:16]

参加物

8

反応物 4

HCID 105592-IodobutaneHCID 24758Sodium hydrideHCID 672603351-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazoleHCID 178506561HCID 178506561、化合物

生成物 1

HCID 672606651-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole収率 88%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-iodo-3-(2-thienyl)-1H-pyrazole (7.1 mmol) in 57 mL dry N,N-dimethylformamide under argon atmosphere at 0° C. was added sodium hydride (8.5 mmol, 60% dispersion in mineral oil) in portions. The reaction mixture was stirred at 0° C. for 15 min, then 2-iodobutane (10.6 mmol) was added dropwise. After 14 h at room temperature, water and MTBE were added to the reaction mixture. The phases were separated and the aqueous phase was extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated to afford 2.7 g of a mixture of 1-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazole and 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole (80:20; 88% yield). The mixture was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100 and cyclohexane:toluene 100:0 to 0:100) to afford 1.16 g 1-sec-butyl-4-iodo-3-(2-thienyl)-1H-pyrazole (48% yield) and 71 mg of 1-sec-butyl-4-iodo-5-(2-thienyl)-1H-pyrazole (3% yield).

後処理

  1. waitAfter 14 h at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with MTBE
  4. washThe combined organic extracts were successively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ba8d8d0749da45dfbde70340c95f5e55
出典データセット
uspto-grants-2014_04
特許番号
US08685974B2

反応ノート

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