Phosphorus oxychloride → 5-(4-Iodo-2-methoxyphenyl)-1,3,4-thiadiazol-2-amine
Reaktionsgleichung
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[NH:13]([C:15](=[S:17])[NH2:16])[NH2:14].P(Cl)(Cl)(Cl)=O>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:17][C:15]([NH2:16])=[N:13][N:14]=2)=[C:4]([O:11][CH3:12])[CH:3]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 78 °C
Versuchsvorschrift
To an ice cooled mixture of 4-iodo-2-methoxybenzoic acid (6.178 g, 22.22 mmol) and hydrazinecarbothioamide (2.43 g, 26.7 mmol) was added phosphorous oxychloride (6.21 mL, 66.7 mmol) slowly. The mixture was heated at 78° C. overnight. After cooling to 0° C., ice water was added and the mixture was vigorously stirred for 1 hour. The resulting precipitate was filtered, washed with water, and re-suspended in saturated NaHCO3(aq) and water (1:1) for 1 hour. The solid was filtered, washed with water, and dried in vacuo to afford the crude compound. The crude material was purified by flash chromatography (MeOH/CH2Cl2) to afford the title compound (1.2 g, 16% yield). MS m/z 334.0 [M+H]+.