2-Aminothiazole → N-[(6-chloro-3-pyridinyl)methylene]-2-thiazolamine
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](C=O)[N:9]=1.Cl[CH2:17]Cl>>[Cl:7][C:8]1[N:9]=[CH:10][C:11]([CH:17]=[N:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:12][CH:13]=1Participants
4
Conditions
- Temperature
- 90 °C
Procedure
2-Aminothiazole (0.75 g, 7.5 mmol) was added to 2-chloropyridine-6-carboxaldehyde (1.0 g, 7.1 mmol) in dichloromethane (25 mL) at room temperature. The suspension was stirred an additional 10 min and then concentrated to dryness under vacuum. The resulting residue was heated to 90° C. on a rotary evaporator with a non-returning bump trap to facilitate water removal. After 30 min the resultant yellow solid was checked by NMR to verify reaction completion (by disappearance of the characteristic aldehyde peak at 10.10 ppm (s, 1H)). The title compound was obtained as a yellow solid (1.55 g) and used in the next step without further purification.