Acetic Acid → 2-Methylbenzo[d]thiazol-7-amine

Reaction equation

[CH3:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C(O)(=O)C>C(O)C.[Fe]>[CH3:1][C:2]1[S:3][C:4]2[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

Procedure

To a solution of 3.8 g of the product from Example 6 and 8.1 g of glacial acetic acid in 56 mL absolute ethanol at reflux temperature was added 3.8 g of iron powder in small portions. The reaction mixture was heated at reflux temperature for about 36 hours, and was then cooled and filtered. The filtrate was concentrated in vacuo and the residue treated with several mL cold water to give a solid. Filtration and drying gave 2.2 g of the title compound as a tan-colored solid, m.p. 100°-101° C.; NMR (CDCl3): δ 2.8 (3H, s), 3.9 (2H, br s), 6.65 (1H, d, J=8 Hz), 7.2 (1H, t, J=8 Hz), 7.5 (1H, d, J=8 Hz).