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

Reaktionsgleichung

Reaktionsgleichung von HRID 1061854
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 22285739N,N-Diethyl-4-[(4-iodo-3,5-dimethyl-pyrazol-1-yl)-(3-methoxy-phenyl)-methyl]-benzamideAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8c3aaa3edc1f4e509c6b2188f9952042
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960609B2

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