Isoquinoline-5-sulphonyl chloride hydrochloride synthesis
- Product Name:Isoquinoline-5-sulphonyl chloride hydrochloride
- CAS Number:105627-79-0
- Molecular formula:C9H7Cl2NO2S
- Molecular Weight:264.12
27655-40-9
105627-79-0
Anhydrous DMF (1.5 mL) was added slowly and dropwise to the suspension formed by stirring 5-isoquinolinesulfonic acid (28.3 g, 135 mmol) with thionyl chloride (150 mL, 2.06 mol) at room temperature and under nitrogen protection. The reaction mixture was heated to reflux and maintained for 2.5 hours. After completion of the reaction, it was cooled to room temperature and subsequently concentrated under reduced pressure to give a light yellow powder. The powder was suspended in anhydrous dichloromethane (200 mL), sonicated, filtered, and dried under reduced pressure at 40 °C to yield a final isoquinoline-5-sulfonyl chloride hydrochloride 29.2 g (111 mmol, 82% yield). The structure of the product was confirmed by 1H NMR (TFA-d): δ 8.48 (t, J = 7.9 Hz, 1H), 9.13-9.14 (m, 2H), 9.29 (d, J = 7.9 Hz, 1H), 9.57 (d, J = 7.0 Hz, 1H), 10.26 (s, 1H).
27655-40-9
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105627-79-0
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Yield: 99%
Reaction Conditions:
with bis(trichloromethyl) carbonate;Triphenylphosphine oxide in ethyl acetate at 50; for 5 h;Temperature;Solvent;
Steps:
1-27 Synthesis of isoquinoline-5-sulfonyl chloride hydrochloride
The isoquinoline-5-sulfonic acid (31.38g, 150mmol),BTC (26.71g, 90mmol), Ph3PO (6.26g, 22.5mmol),Add ethyl acetate (300mL) to a 500mL reaction flask,Heat to 50°C for 5 hours,Down to room temperature,Add dichloromethane (150mL) and stir,Suction filtration to obtain a white solid,Vacuum dry at 4050,39.22g of solid was obtained,The yield is 99%,HPLC content is 99.99%.After the filtrate is concentrated, Ph3PO is precipitated at low temperature.After washing with a small amount of petroleum ether,Suction filtration,Ph3PO (6.23g) obtained by drying can be reused.
References:
Zhejiang University of Technology;Weng Yiyi;Li Nanhui;Sun Chen CN111909088, 2020, A Location in patent:Paragraph 0046-0099