Reaktion #42278

Reaktionsgleichung

Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate

hydrochloric acid

sulfur dioxide

Sodium nitrite

→

title compound

Methyl 3-(chlorosulfonyl)-5-[(dipropylamino)carbonyl]- benzoate

Lösungsmittel

water

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture is extracted with ethyl acetate
2. 2
   SonstigeThe organic phase is separated
3. 3
   Waschenwashed with saturated sodium bicarbonate, water, and saline
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

Methyl 3-amino-5-[(dipropylamino)carbonyl]benzoate (XXXI, PREPARATION 10, 1.11 g, 4 mmol) is added to a mixture of water (5 mL) and concentrated hydrochloric acid (1 mL). Sodium nitrite (0.276 g, 4 mmol) is added to the mixture slowly at 0 degrees C. The mixture is then added to an acetic acid solution (5 mL) of CuCl2.2H2O saturated with sulfur dioxide. The mixture is stirred for 0.5 hours and poured into ice water. The mixture is extracted with ethyl acetate. The organic phase is separated and washed with saturated sodium bicarbonate, water, and saline and dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound, NMR (300 MHz, CDCl3) delta 8.69, 8.38, 8.20, 4.01, 3.49, 3.14, 1.72, 159, 1.01 and 0.79; MS (ESI+) for C15H20ClNO5S m/z (M+H)+=362.2

Quelle