1,2-Dichloroethane → N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]-3-methoxybenzamide

HRID 1012083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012083
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[C:21]1[C:25]([NH2:26])=[CH:24][NH:23][N:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CS(C)=O.O>[NH:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]=[C:13]1[C:21]1[C:25]([NH:26][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:24][NH:23][N:22]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 114613-Methoxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 178508052HCID 178508052, Verbindung

Produkt 1

HCID 178490490N-[3-(2H-Benzimidazol-2-ylidene)-2,3-dihydro-1H-pyrazol-4-yl]-3-methoxybenzamideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxybenzoic acid (84 mg, 0.55 mmol), 3-(1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.50 mmol), EDC (116 mg, 0.60 mmol) and HOBt (81 mg, 0.60 mmol) was stirred at ambient temperature in DMSO (3 ml) for 20 h. The reaction mixture was poured into water (30 ml) and the resultant solid was collected by filtration and purified by flash column chromatography [SiO2, (dichloromethane 120 ml, methanol 15, acetic acid 3 ml, water 2 ml (DMAW 120)] to yield N-[3-(1H-Benzimidazol-2-yl)-1H-pyrazol-4-yl]-3-methoxy-benzamide as a pale pink-gray solid (21 mg, 13%). (LC/MS: Rt 3.81, [M+H]+ 334.03).

Aufarbeitung

  1. filtrationthe resultant solid was collected by filtration
  2. custompurified by flash column chromatography [SiO2

Quellen und Nachweise

ORD-Eintrag
ord-0db6d0ba4466492dbd890bdfb0092f19
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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