Dimethylformamide → 2-Chloro-N-cyclopropyl-5-(3-methoxy-propyl)-benzamide

Participants

Reaction Conditions

Reaction Steps

2-Chloro-N-cyclopropyl-5-(3-methoxy-propenyl)-benzamide (12.6 g, 47.6 mmol) was dissolved in dry toluene (650 mL). Dry DMF (70 mL) was added, and the mixture was heated to 110° C. Benzensulfonyl hydrazine (24.5 g, 143 mmol) was added in three portions over 3 h. The mixture was heated for a total time of 3 h, and allowed to cool to rt. The solvents were removed under reduced pressure, and the residue was diluted with Et2O. The mixture was washed with water, and the aq. phase was extracted back with Et2O (3×). The combined org. extracts were washed with water, and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:9→1:4→1:3→1:1) yielded the title compound (10.0 g, 78%). LC-MS: tR=0.83 min; ES+: 268.19.

Provenance & Evidence