Triethylamine → Ethanethioic acid, S-[(2-methyl-2H-tetrazol-5-yl)methyl] ester

Temperature

0 °C

To a solution of 5-hydroxymethyl-2-methyltetrazole (1.83 g, 11.7 mmol) in dry dichloromethane (25 mL) at 0° C. was added methanesulfonyl chloride (1.47 g, 12.9 mmol) followed by triethylamine (1.30 g, 12.9 mmol) added dropwise over five min. The mixture was stirred at 0° C. for 1 h, and then treated with a solution of potassium thioacetate (1.60 g, 14.0 mmol) in dry N,N-dimethylformamide (10 mL). The resulting gel was stirred at 0° C. for 3 h. The reaction mixture was diluted with dichloromethane (200 mL), washed with brine (20 mL) and dried over anhydrous sodium sulfate. Evaporation of the solvent under vacuum and chromatography of the resulting oil over silica gel (2×15 cm, eluting with dichloromethane and dichloromethaneacetone 5%) gave the title compound as a clear oil: 1.31 g (65%); ir (film) νmax : 1696 cm-1 (C=O of thioester); 1Hmr (CDCl3) δ: 2.43 (3H, s, SAc), 4.36 (3H, s, 2-CH3), 4.38 ppm (2H, s, 5-CH2).

1. additionadded dropwise over five min
2. stirringThe resulting gel was stirred at 0° C. for 3 h
3. washwashed with brine (20 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. customEvaporation of the solvent under vacuum and chromatography of the resulting oil over silica gel (2×15 cm, eluting with dichloromethane and dichloromethaneacetone 5%)

ORD record

ord-feef976f298742e4b55d15a60ddb9091

Source dataset

uspto-grants-1987_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04644061