3,5-Dimethyl-4-iodo-1H-pyrazole → N,N-Diethyl-4-[(4-iodo-3,5-dimethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-methyl]-benzamide

HRID 1061854

反応式

HRID 1061854 の反応式
Cl[CH:2]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[C:3]1[CH:15]=[CH:14][C:6]([C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.[I:24][C:25]1[C:26]([CH3:31])=[N:27][NH:28][C:29]=1[CH3:30]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[CH2:10]([N:9]([CH2:12][CH3:13])[C:7](=[O:8])[C:6]1[CH:14]=[CH:15][C:3]([CH:2]([N:27]2[C:26]([CH3:31])=[C:25]([I:24])[C:29]([CH3:30])=[N:28]2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:4][CH:5]=1)[CH3:11]

参加物

5

反応物 2

HCID 971153,5-Dimethyl-4-iodo-1H-pyrazoleHCID 99968274-[(Chloro)(3-methoxyphenyl)methyl]-N,N-diethylbenzamide

生成物 1

HCID 22285739N,N-Diethyl-4-[(4-iodo-3,5-dimethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-methyl]-benzamide収率 96.1%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

To a stirring solution of 4-[Chloro-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide (1.11 g, 3.32 mmol) in 20 Ml CH3CN was added 4-iodo-3,5-dimethyl pyrazole (1.64 g, 7.40 mmol) and tetra-n-butyl ammonium iodide (619 mg, 1.68 mmol). The mixture was heated to reflux for 24 h, cooled to room temperature and concentrated under reduce pressure. The crude oil was purified by flash chromatography on a 3×20 cm column, eluting with 30% ethyl acetate/hexanes, collecting 8 mL fractions. The product containing fractions were collected and concentrated under reduce pressure to give the desired product (1.65 g, 96%) as a clear yellow oil. 400 MHz 1H NMR (CDCl3) δ 7.31 (d, J=8.1 Hz, 2H), 7.19-7.24 (m, 1H), 7.13 (d, J=8.3 Hz, 2H), 6.79-6.82 (m, 1H), 6.68-6.70 (m, 2H), 6.54 (s, 1H), 3.71 (s, 3H), 3.50 (br s, 2H), 3.23 (br s, 2H), 2.21 (s, 3H), 2.18 (s, 3H), 1.21 (br s, 3H), 1.08 (br s, 3H); 75 MHz 13C NMR (CDCl3), δ 170.8, 159.7, 149.8, 141.2, 140.3, 140.1, 136.7, 129.6, 128.5, 126.6, 120.8, 114.4, 113.2, 66.5, 55.3, 43.3, 39.3, 14.4, 12.6; MS (M+1) 518.0.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated
  4. customThe crude oil was purified by flash chromatography on a 3×20 cm column
  5. washeluting with 30% ethyl acetate/hexanes
  6. customcollecting 8 mL fractions
  7. additionThe product containing fractions
  8. customwere collected
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-8c3aaa3edc1f4e509c6b2188f9952042
出典データセット
uspto-grants-2005_11
特許番号
US06960609B2

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