[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.[N:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)=[N+:11]=[N-:12].S(Cl)(Cl)=O.C(N(CC)CC)C>O1CCCC1>[N:10]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:1][CH:2]2[CH2:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]2)=[O:18])=[CH:20][CH:21]=1)=[N+:11]=[N-:12]This example describes the preparation of an azidoaryl-substituted cyclooctene by reaction of an acid chloride-substituted phenyl azide with 5-aminocyclooctene. The reactions are illustrated in Scheme 4. 4-Azidobenzoic acid was converted to the corresponding acid chloride (10) with thionyl chloride and triethylamine in dry tetrahydrofuran. An excess of 5-aminocyclooctene was then introduced to the solution of the acid chloride at 0° C. to form the azidoaryl-substituted cyclooctene, 4-azido-N-4-cycloocten-1-yl-benzamide (9), which was purified by recrystallization from diethyl ether/hexane in 73% yield. The product was characterized by proton and carbon-13 nuclear magnetic resonance spectroscopy (1H and 13C NMR), as well as Fourier Transform Infrared (FTIR) spectroscopy. Key features in the characterization of 4-azido-N-4-cycloocten-1-yl-benzamide included the presence of the amide carbonyl in the 13C NMR spectrum at 165.1 parts per million (ppm), and a characteristic azide signal in the IR spectrum at 2120 reciprocal centimeters (cm−1).
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