1-Pyrrolidineethanamine → 6-Nitro-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-6-nitrobenzothiazole (250 mg, 1.16 mmol) and 2-pyrrolidin-1-yl-ethylamine (0.59 mL, 4.66 mmol) was heated at 100° C. for 4 hours then at 60° C. for 16 hours. After this time, the reaction mixture was filtered and the precipitate was washed with 2×5 mL of H2O. The solid was subjected to silica gel column chromatography (7.5% MeOH:92.5% CH2Cl2) to give the title compound as a yellow residue. Yield: 20.6%, 1H-NMR (DMSO-d6): δ 8.80 (br s, 1H); 8.70 (d, 1H, J=2.4 Hz); 8.11 (dd, 1H, J=6.8, 2.4 Hz); 7.47 (d, 1H, J=8.8 Hz); 3.58 (m, 2H); 2.60 (m, 6H); 1.73 (m, 2H).

Provenance & Evidence