C(N(CC)CC)C.[C:8]1([CH3:19])[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16](O)=[O:17])=[CH:10][CH:9]=1.ClC(OCC)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>C(#N)C.O>[C:8]1([CH3:19])[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([N:26]=[N+:27]=[N-:28])=[O:17])=[CH:10][CH:9]=1
Triethylamine (8.5 mL, 60 mmol) was added slowly into the mixture of 3-p-tolyl-acrylic acid (8.3 g, 50 mmol) in 40 mL of acetonitrile followed by drop-wise addition of ethyl chloroformate (5.3 mL, 55 mmol) at 0° C. The solution was stirred for 2 h at this temperature. Sodium azide (6.5 g, 100 mmol) in 50 mL of water was added slowly to the above solution at 0° C. and the mixture was kept stirring for 1 h. Cold water was added and the precipitate was filtered and washed with cold water. The solid product (7.66 g, 82% yield) was obtained after being dried under vacuum. 1H-NMR (300 MHz, CDCl3) δ 7.72 (d, 1H), 7.44 (d, 2H), 7.21 (d, 2H), 6.38 (d, 1H), 2.39 (s, 3H).
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