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ChemicalBook CAS DataBase List 3-(HYDROXYMETHYL)-2-BENZOTHIAZOLINONE
72679-97-1

3-(HYDROXYMETHYL)-2-BENZOTHIAZOLINONE synthesis

3synthesis methods
-

Yield: 94%

Reaction Conditions:

with formaldehyd in n-heptane;water

Steps:

3 EXAMPLE 3 STR18
EXAMPLE 3 STR18 To a stirred slurry containing 30.2 (0.2 mol.) of 2-hydroxybenzothiazole and 40 ml. of methyl alcohol was added 32 ml. of 40% aqueous formaldehyde in one portion. Upon heating the stirred reaction mixture to 63° C., a solution formed. The solution was then heated at reflux (78°-80° C.) for 30 minutes. To the stirred solution at 80° C., was added hot water (60 ml.) until the solution appeared cloudy. The stirred reaction mixture was cooled to 0° C. and then stirred at 0°-10° C. for 15 minutes. A solid was collected by filtration, washed with 100 ml. of heptane and air-dried at 25°-30° C. to yield 3-hydroxymethyl-2-benzothiazolinone (94% yield) (Compound 14) having a melting point of 101°-103° C. and the following analysis: Anal. Calc'd for C8 H7 NO2 S: N, 7.73; S, 17.70. Found: N, 7.95; S, 17.89.

References:

Monsanto Company US4578477, 1986, A

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