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5-(4-CHLOROPHENYLTHIOMETHYL)TETRAZOLE synthesis
- Product Name:5-(4-CHLOROPHENYLTHIOMETHYL)TETRAZOLE
- CAS Number:18527-31-6
- Molecular formula:C8H7ClN4S
- Molecular Weight:226.69
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, JHH = 8.0 Hz), 7.31 d (2H, Ar, JHH = 8.0 Hz). 13C NMR spectrum, δC, 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]