Reaction #1178464

Reaction equation

thiourea

1,4-benzoquinone

→

2-amino-1,3-benzothiazol-6-ol

Solvents

ethanol

hydrochloric acid

ethanol

Conditions

Workup

1. 1
   Concentrationconcentrated to dryness
2. 2
   OtherThe residue was triturated with hot acetonitrile
3. 3
   Filtrationthe resulting solid was filtered
4. 4
   Otherdried

Procedure

The intermediate 2-amino-1,3-benzothiazol-6-ol was prepared according to a slightly modified literature procedure by Lau and Gompf: J. Org. Chem. 1970, 35, 4103-4108. To a stirred solution of thiourea (7.6 g, 0.10 mol) in a mixture of 200 mL ethanol and 9 mL concentrated hydrochloric acid was added a solution of 1,4-benzoquinone (21.6 g, 0.20 mol) in 400 mL of hot ethanol. The reaction was stirred for 24 hours at room temperature and then concentrated to dryness. The residue was triturated with hot acetonitrile and the resulting solid was filtered and dried.

Source