2-Methylbenzothiazole → Benzothiazolium, 3-(2-hydroxyethyl)-2-methyl-, bromide (1:1)

A solution of 2-methylbenzothiazole (5.87 g) and bromoethanol (49.2 g) were stirred in an oil bath at 110° C. for 18 hours. Added ethyl acetate (100 mL) to the reaction mixture and decanted. The residual solid was then dissolved in methanol (50 mL) and precipitated with ethyl acetate (300 mL). The solid was again recrystallized from methanol-ethyl acetate (15 mL/150 mL), washed with ethyl acetate (2×25 mL) and dried in an oven under high vacuum at 50° C. overnight. The yield was 4.21 g (39%). TLC (silica gel, 4:1 methylene chloride-methanol) Rf=0.34.

1. customAdded ethyl acetate (100 mL) to the reaction mixture and decanted
2. dissolutionThe residual solid was then dissolved in methanol (50 mL)
3. customprecipitated with ethyl acetate (300 mL)
4. customThe solid was again recrystallized from methanol-ethyl acetate (15 mL/150 mL)
5. washwashed with ethyl acetate (2×25 mL)
6. customdried in an oven under high vacuum at 50° C. overnight

ORD record

ord-3996b4f376034c20a93a45a4cf215338

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06551831B2