N(OCCC(C)C)=O.[CH3:9][C:10]1[N:11]=[C:12](N)[S:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[ClH:25]>CC#N.[Cu](Cl)Cl>[Cl:25][C:12]1[S:13][C:14]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:10]([CH3:9])[N:11]=1Isoamyl nitrite (3.5 ml, 25 mmol) is added to a stirred suspension/solution of anhydrous copper (II) chloride (2.75 g, 20 mmol) in dry methylcyanide (50 ml). 4-Methyl-5-(4-nitro-phenyl)-thiazol-2-ylamine (25a) (4.0 g, 17 mmol) is then added over 30 minutes. The resulting slurry is stirred at room temperature for 1 hour then heated at 70° C. for 30 minutes. After cooling to room temperature the black solution is poured into 4M hydrochloric acid (200 ml). The product is extracted with ethyl acetate, dried (MgSO4) and the solvent removed to give the title compound as an orange powder (3.13 g). MH+ (TOF, ES+): 255.0
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