Preparation of 2-pyridine sulfonate diethylamide_industrial additives

Preparation background and overview of 2-pyridine sulfonate diethylamide

2-Pyridine sulfonate diethylamide is an organic intermediate. It can be prepared from 2-mercaptopyridine as the starting material (2-pyridyl)sulfonyl chloride, and then acylated with N, N-diethylamine. prepared.

Preparation of 2-pyridine sulfonate diethylamide

Preparation step 1 of 2-pyridine sulfonate diethylamide

To a solution of 2-mercaptopyridine (2.0 g, 17.2 mmol, 1 equivalent) in 50 mL of concentrated sulfuric acid, aqueous sodium hypochlorite solution (112 mL, 12%) was added dropwise at 0°C. After the addition was complete, the reaction mixture was stirred for an additional 30 minutes at 0°C and then diluted with water (30 mL) and CH₂Cl₂ (30 mL). The aqueous layer was extracted with CH₂Cl₂ (2×20mL), and the combined organic layers were treated with Na₂SO₄Dry, filter and concentrate under reduced pressure to obtain (2-pyridyl)sulfonyl chloride as colorless oil.

Potassium trifluoroborate

Preparation step 2 of 2-pyridinesulfonic acid diethylamide

Then, the crude product was diluted in 23 mL of anhydrous CH₂Cl₂, and 5.4 mL of N,N- was added to the mixture at 0°C. Diethylamine (3 equiv, 51.7 mmol). The red solution was stirred at room temperature for 12 hours, then poured into water and extracted with EtOAc. The combined organic layers were dried over Na₂SO₄, filtered, and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (EtOAc/hexane 7:3) to afford 2-pyridine sulfonate diethylamide as a colorless oil (2.440 g, 11.40 mmol) in 66% yield. IR (NaCl) 3052, 2976, 2937, 2839, 1453, 1577, 1426, 1332, 1151, 1018, 780, 746cm^-1;¹HNMR (CDCl₃, MHz): δ8.57 (d, 1H, J=4.8Hz), 7.84 (d, 1H, J=7.6Hz), 7.80 (td, 1H, J=1.6 and 7.7H basic Copper carbonate z), 7.42 (ddd, 1H, J=1.4, 4.8 and 7.2Hz), 3.29 (q, 4H, J=7.1Hz), 1.03 (t, 6H, J=7.1Hz);¹³CNMR (CDCl₃, 100MHz): δ158.3 (C), 149.8 (CH), 137.8 (CH), 126.2 (CH), 122.0 (CH), 42.7 (2xCH2), 14.2 (2xCH3); MS (ESI) m/z 215 [M+H⁺]; HRMS (ESI): Calculated value for C9H15N2O2S: 215.0865; Found value: 215.0865. Actual measurement: 215.0854.