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ChemicalBook CAS DataBase List S-METHYL-N,N-DIETHYLTHIOCARBAMATE
37174-63-3

S-METHYL-N,N-DIETHYLTHIOCARBAMATE synthesis

9synthesis methods
-

Yield:37174-63-3 97%

Reaction Conditions:

in tetrahydrofuran;lithium hydroxide monohydrate; for 3 h;Inert atmosphere;Reflux;

Steps:

1-1 Example 1-1: /V,/V-diethyl-l-(methylsulfide)methanamide

To a solution of 200 g of 21 wt% of aqueous sodium methane thiolate solution (599 mmol) was added a solution of /V,/V-diethyl carbamoyl chloride (68.3mL, 539 mmol) in THF (600mL), followed by 4.7g (2 mol%) of tetrahexylammonium chloride. The biphasic mixture was stirred rapidly and heated to reflux under nitrogen capturing excess sulfide gasses with a bleach trap. After reflux for 3 h, the solution was cooled to rt. The biphasic reaction was extracted with 1 L of diethyl ether, and the organic phase was washed with brine and dried over sodium sulfate. After evaporation under reduced pressure, the crude oil was subjected to chromatography (Sorbtech silica gel 60; dichloromethane) to afford A,A-diethyl- 1 -(met hylsul fide) met hanamide Example 1-1 as a light yellow oil (76.8 g; 97%). NMR (400 MHz, CDCb): d 3.36 (br s, 4H, 2 x CH2), 2.30 (s, 3H, SCH3), 1.15 (br s, 6H, 2 x CH3).

References:

WO2022/115742,2022,A1 Location in patent:Page/Page column 123-124

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