4-Chlorobenzoyl chloride → N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-4-chlorobenzamide

N1-(Benzo [d]isothiazol-3-yl)ethane-1,2-diamine (50 mg, 0.26 mmol) was dissolved in anhydrous dichloromethane (5 mL) with diisopropylethylamine (50 μL, 0.28 mmol). The solution was cooled on an ice-water bath and then a solution of 4-chlorobenzoyl chloride (36 μL, 0.28 mmol) in dichloromethane (0.5 mL) was added dropwise. The reaction mixture was allowed to stir for 2 h while warming to room temperature. The solution was washed with water, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure. Purification by column chromatography, on silica gel, eluting with a mixture of 25% ethyl acetate in hexanes, and selected fractions were combined and concentrated under reduced pressure to yield N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)-4-chlorobenzamide as a white solid, (50 mg). 1H NMR (300 MHz, DMSO-d6): 8.7 (broad s, 1H), 8.1 (d, 1H), 7.9 (m, 3H), 7.5 (m, 4H), 7.4 (m, 1H), 3.6 ppm (m, 4H). MW=332 confirmed by LC-MS, tr=3.89 min (Method B) MH+=333.

1. temperatureThe solution was cooled on an ice-water bath
2. washThe solution was washed with water
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationthe filtrate concentrated under reduced pressure
6. customPurification by column chromatography
7. washon silica gel, eluting with a mixture of 25% ethyl acetate in hexanes
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-d219bdd5b3694d0aad628536c83e3954

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07776847B2