Sodium Hydroxide → 6-Methylbenzo[d]thiazol-5-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.78 g of 6-methyl-5-nitrobenzothiazole and 3.62 g of stannous chloride dihydrate in 25 mL of ethanol is heated to 65° C. for 4 hours. The cooled reaction mixture is poured into 10 mL of 50% sodium hydroxide and 45 mL of brine and extracted with ether (4×35 mL). The combined organic layers are washed with brine, dried over sodium sulfate and rotary evaporated. The residue is purified by flash column chromatography on silica gel, eluting with 15% ethyl acetate/hexanes to provide 0.45 g of 5-amino-6-methylbenzothiazole as a yellow solid.

Provenance & Evidence