2(3H)-Benzothiazolethione,5-(hydroxymethyl)-(9CI) synthesis

Yield:-

Reaction Conditions:

with hydrogenchloride in tetrahydrofuran;

Steps:

P.10 5-HYDROXYMETHYL-2-THIOXO-2,3-DIHYDROBENZOTHIAZOLE STR135

PREPARATIVE EXAMPLE 10 5-HYDROXYMETHYL-2-THIOXO-2,3-DIHYDROBENZOTHIAZOLE STR135 A solution of 5.04 g (23.9 mmol) of 2-thioxo-2,3-dihydrobenzothiazole-5-carboxylic acid in 25 ml of anhydrous tetrahydrofuran was stirred and heated to reflux, and 2.0 g of lithium aluminum hydride in 25 of anhydrous tetrahydrofuran was added carefully. After refluxing for two hours, the solution was cooled and added carefully to 500 ml of chilled 2N HCl. This mixture was extracted 3 times with 200 ml of ethyl acetate, and the combined organics were dried over magnesium sulfate and evaporated under reduced pressure to yield 3.67 g of the title compound. ¹ H NMR (DMSO-₆, 500 MHz) δ7.59 (d, ArH), 7.29 (s, ArH), 7.19 (d, ArH), 4.52 (s, ArCH₂ OH). ¹³ C NMR (DMSO-d₆, 500 MHz) δ190.4, 142.8, 141.8, 127.8, 122.9, 121.7, 110.5 & 62.7.

References:

US5496816,1996,A