[Cl:1][C:2]1[C:3]([S:10][CH3:11])=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.[N+:12]([CH2:15][CH2:16][CH3:17])([O-])=[O:13].C1(N=C=O)C=CC(N=C=O)=CC=1.O>C(N(CC)CC)C.C1C=CC=CC=1>[CH2:16]([C:15]1[CH:9]=[C:8]([C:6]2[CH:5]=[N:4][C:3]([S:10][CH3:11])=[C:2]([Cl:1])[CH:7]=2)[O:13][N:12]=1)[CH3:17]
A mixture of 3-chloro-5-ethynyl-2-methylthiopyridine (0.5 g, 2.72 mmol), 1-nitropropane (0.24 g, 0.27 mmol), 1,4-phenylenediisocyanate (1.3 g, 7.93 mmol) and triethylamine (5 drops) in benzene (20 mL) was heated under reflux with stirring for 8 hours, and allowed to stir at room temperature overnight. Water (1 mL) was added and the mixture stirred at room temperature for 2 hours. It was filtered through Celite, dried over anhydrous sodium sulphate and evaporated under reduced pressure. Recrystallisation of the residue from hexane gave the desired product (0.33 g, 48%) as a cream solid, melting point. 78-80° C.
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