2-Amino-6-methoxybenzothiazole → 2-Amino-6-benzothiazolol

Temperature

135 °C

To a vial equipped with a magnetic stir bar, was added 2-amino-6-methoxybenzthiazole (1.0 g, 5.55 mmol, 1.0 equiv). To the vial, was added 48% HBr in AcOH (1.5 mL) and 45% HBr aqueous solution (1.5 mL). The vial was sealed and heated to 135° C. for 3 h until LCMS indicated completion of the reaction. The mixture was allowed to rt. The solid precipitate was filtered, washed with water (2 mL), diethyl ether (2 mL×2) and dried in vacuo to afford an off white solid GC-4-49 (1.0 g, 73%). 1H-NMR (400 MHz, DMSO) δ: 9.42 (br, 2H), 7.31 (m, 2H), 6.87 (dd, J=8.8 Hz, 2.4 Hz, 1H); MS: 248.1 [M+H+—HBr].

1. customTo a vial equipped with a magnetic stir bar
2. customThe vial was sealed
3. customcompletion of the reaction
4. customwas allowed to rt
5. filtrationThe solid precipitate was filtered
6. washwashed with water (2 mL), diethyl ether (2 mL×2)
7. customdried in vacuo
8. customto afford an off white solid GC-4-49 (1.0 g, 73%)

ORD record

ord-b043463bd35d4be781b0ee71718a03a5

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420052B2