Sodium Bicarbonate → N2-(1-Phenylethyl)-1,3-benzothiazole-2,7-diamine
Reaction equation
[N+:1]([C:4]1[C:12]2[S:11][C:10]([NH:13][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:16]1([CH:14]([NH:13][C:10]2[S:11][C:12]3[C:4]([NH2:1])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)[CH3:15])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 0.165 g (0.55 mmol) of 7-nitro-N-(1-phenylethyl)-1,3-benzothiazol-2-amine in 10 mL of DMF was added 0.62 g (2.8 mmol) of stannous chloride dihydrate. The reaction was heated to 80° C. for 48 h and neutralized with saturated sodium bicarbonate. The mixture was filtered through celite and extracted with ethyl acetate. The extracts were dried in vacuo and purified by flash chromatography eluting with a 50-75% ethyl acetate/hexanes gradient mixture to give 0.016 g (11%) of the title compound as a light yellow solid.