Reaction #9674

Reaction equation

6-amino-m-cresol

potassium O-ethyl xanthate

HCl

→

6-methyl-1,3-benzoxazole-2(3H)-thione

Solvents

pyridine

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 2 h
3. 3
   OtherThe solid was collected
4. 4
   Washwashed with water
5. 5
   Otherdried in the hood overnight

Procedure

A mixture of 6-amino-m-cresol (593.7 mg, 4.82 mmol) and potassium O-ethyl xanthate (850 mg, 5.30 mmol) in pyridine (10 mL) was stirred and heated to reflux for 2 h. It was cooled to rt, poured into a mixture of ice-water (40 mL), and concentrated HCl (4 mL). The solid was collected, washed with water, and dried in the hood overnight and then in a vacuum oven at 45° C. for 3 h. The product 6-methyl-1,3-benzoxazole-2(3H)-thione was obtained as beige powder (735 mg, yield 92.3%). 1H NMR (300 MHz, DMSO-d6) δ 7.10 (s, 1 H), 7.03 (d, 2 H), 2.42 (s, 3H); LC-MS ret. time 2.37 min (method 2), m/z 166.0 (MH+).

Source