5-(4-CHLOROPHENYLTHIOMETHYL)TETRAZOLE synthesis

Yield:18527-31-6 86%

Reaction Conditions:

Stage #1: chloroacetonitrile;p-Chlorothiophenolwith potassium carbonate in propan-1-ol at 40; for 2 h;
Stage #2: with sodium azide;zinc(II) chloride in propan-1-ol at 95; for 1 h;

Steps:

5-[(4-Chlorophenylthio)methyl]-1H-tetrazole (5).

To a solution of 7.0 mmol of 4-chlorothiophenol 3 in 25 mL of n-PrOH were added 7.0 mmol of 2-chloroacetonitrile and 7.0 mmol of K₂CO₃. The reaction mixture was stirred at 40°C for 2 h. Then 10.4 mmol of NaN₃ and 10.4 mmol of ZnCl₂ were added, and the mixture was stirred at 95°C for 1 h. The reaction product was isolated in the same manner as in the synthesis of 5-alkylsulfanyl-1H-tetrazoles. Yield 1.35 g (86%), colorless crystals, mp 159-161°C (H₂O-EtOH, 1 : 2). IR spectrum, ν, cm^-1: 2847 br (CH₂), 1571 m (C=N), 1473 s (Ph), 1093 m (C-N), 744 w (C-S). ¹H NMR spectrum, δ, ppm: 4.39 s (2H, CH₂), 7.25 d (2H, Ar, J_HH = 8.0 Hz), 7.31 d (2H, Ar, J_HH = 8.0 Hz). ¹³C NMR spectrum, δ_C, ppm: 26.1 (CH₂), 129.4 (Ar), 131.5 (Ar), 132.5 (Ar), 133.4 (Ar), 154.9 (C-N). Found, %: C 42.44; H 3.00; N 24.67; S 14.30. C₈H₇ClN₄S. Calculated, %: C 42.39; H 3.11; N 24.72; S 14.15.

References:

Myznikov;Vorona;Artamonova;Zevatskii, Yu. E. [Russian Journal of General Chemistry,2017,vol. 87,# 6,p. 1313 - 1316][Zh. Obshch. Khim.,2017,vol. 87,# 6,p. 1041 - 1044,4]