Methanol → N-(5-(methoxymethyl)pyridin-2-yl)-5-thiocyanatothiazol-2-amine
Reaction equation
[S:1]([C:4]1[S:8][C:7]([NH:9][C:10]2[N:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)=[N:6][CH:5]=1)[C:2]#[N:3].[CH3:18]O>O=P(Cl)(Cl)Cl>[CH3:18][O:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7]2[S:8][C:4]([S:1][C:2]#[N:3])=[CH:5][N:6]=2)=[N:15][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
(6-(5-Thiocyanatothiazol-2-ylamino)pyridin-3-yl)methanol (0.094 g, 0.356 mmol) was dissolved in POCl3 (3 mL) and the reaction was heated at 85° C. for 3 hours. POCl3 was then evaporated and the resulting oil was washed with water to give a gummy solid. Methanol (10 mL) was added to the solid and the resulting suspension was stirred at 23° C. for over a month. Methanol was evaporated to almost dryness and water was added to precipitate the oil. The resulting solid was filtered and dried under vacuum to give the crude title material (0.109 g, quant.) which was used as such in the next reaction. HPLC ret. time (Condition A): 1.603 min. LC/MS (M+H)+: 279.