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 1061854노트

반응식

HRID 1061854 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8c3aaa3edc1f4e509c6b2188f9952042
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960609B2

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