Dichloromethane → 1H-Imidazole-2-acetonitrile, 5-((3,5-dichlorophenyl)thio)-1-methyl-4-(1-methylethyl)-
Reaktionsgleichung
Cl[CH2:2][C:3]1[N:4]([CH3:20])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[C-:21]#[N:22].[K+].C(Cl)Cl>CN(C)C=O>[Cl:19][C:14]1[CH:13]=[C:12]([S:11][C:5]2[N:4]([CH3:20])[C:3]([CH2:2][C:21]#[N:22])=[N:7][C:6]=2[CH:8]([CH3:10])[CH3:9])[CH:17]=[C:16]([Cl:18])[CH:15]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 72.5 °C
Versuchsvorschrift
In 13.6 ml of dry dimethylformamide was dissolved 4.75 g (13.6 mmol)of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (28a)and 1.0 g of potassium cyanide (97.5%), and the mixture was stirred with heating at 70 to 75° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and to the residue, water was added. The mixture was extracted with diethyl ether, and the organic layer was washed with water 3 times and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was fractionated by silica gel chromatography (ethyl acetate:methylene chloride=1:9 to 4)to obtain 2.43 g of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetonitrile (Compound I-80a)(yield 53%). mp 103-105° C.
Aufarbeitung
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionto the residue, water was added
- extractionThe mixture was extracted with diethyl ether
- washthe organic layer was washed with water 3 times
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-9c7e86dd6c2b431e99e30a2f0635c7bf
- Quelldatensatz
- uspto-grants-1999_06
- Patentnummer
- US05910506
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