Benzenemethanamine, N-butyl-3,4-dichloro- → N-Butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide

HRID 528936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528936
[Cl:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][NH:5][C:6]=1[CH3:7].[Cl:11][C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:17]([N:16]([CH2:15][C:14]1[CH:21]=[CH:22][C:23]([Cl:24])=[C:12]([Cl:11])[CH:13]=1)[C:8]([C:3]1[C:2]([Cl:1])=[C:6]([CH3:7])[NH:5][N:4]=1)=[O:10])[CH2:18][CH2:19][CH3:20]

Komponenten

3

Edukt 2

HCID 485439Benzenemethanamine, N-butyl-3,4-dichloro-2×HCID 176889814-Chloro-3-methyl-1H-pyrazole-5-carboxylic acid

Produkt 1

HCID 71062158N-Butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamideAusbeute 48 %

Versuchsvorschrift

Following a procedure analogous to that for the synthesis of Intermediate 168A, 4-chloro-5-methyl-1H-pyrazole-3-carboxylic acid (1.50 g, 9.32 mmol) and N-(3,4-dichlorobenzyl)butan-1-amine (Intermediate 126, 2.16 g, 9.32 mmol) provided the title compound (1.67 g, 48%) as a colorless oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 7.50-7.32 (m, 2H), 7.24-7.06 (m, 1H), 4.79-4.55 (m, 2H), 3.47-3.26 (m, 2H), 2.34-2.19 (m, 3H), 1.71-1.46 (m, 2H), 1.35 (br s, 1H), 1.18 (br s, 1H), 0.93 (d, J=6.4 Hz, 1.5H), 0.81 (d, J=6.8 Hz, 1.5H); MS(ESI+) m/z 376.0 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-5686d4e0985a440fa61a5c1efcb0b1ea
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

Notizen zur Reaktion

Wird geladen…