CC1C=CC(S([CH2:11][N+:12]#[C-:13])(=O)=O)=CC=1.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=O.[Na].O1CC[N:25]=C1>C(O)C>[NH:12]1[CH:13]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[N:25]=[CH:11]1This compound known in the literature was made by an alternative route in analogy to Heterocycles 1994, 39 (1), 139: Tosylmethylisocyamide (TOSMIC) (3.57 g) was suspended in ethanol (50 ml) and 2-picolinealdehyde (2.0 g) was added. Sodium cyamide (92 mg) was added in one portion at 15° C. and the mixture was allowed to stir—the internal temperature rose to 26° C. and a clear solution was obtained. The mixture was cooled again to 15° C. and the intermediate oxazoline derivative precipitated. The suspension was filtered and the solid intermediate washed with ether/hexanes 1:1 and dried in vacuo (yield: 4.77 g).
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