Reacción #4234

Ecuación de reacción

2-(chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

pyrrolidine

KBr

→

2-(1-Pyrrolidinylmethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, hydrochloride salt

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroVolatiles were removed under vacuum
2. 2
   OtroSolvent was removed
3. 3
   workup.ADDITIONthe water (15 ml) was added
4. 4
   workup.ADDITIONthe pH was adjusted to 6.0 by addition of dilute hydrochloric acid
5. 5
   TemperaturaCooling
6. 6
   Otroscratching produced a white solid which
7. 7
   Otrowas collected
8. 8
   Otrodried
9. 9
   Otroto give 488 mg, m.p. 117°-123°
10. 10
    OtroA 400 mg sample was crystallized from acetonitrile
11. 11
    Otroto give 269 mg
12. 12
    Otroabsorption bands

Procedimiento

A slurry of 2-(chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.00 g) in dimethylformamide (5 ml) was contacted with pyrrolidine (0.45 ml) and stirred for 3.5 hrs. Volatiles were removed under vacuum and the residue was taken up in methanol. Solvent was removed and the water (15 ml) was added and the pH was adjusted to 6.0 by addition of dilute hydrochloric acid. Cooling and scratching produced a white solid which was collected and dried to give 488 mg, m.p. 117°-123°. A 400 mg sample was crystallized from acetonitrile to give 269 mg. m.p. 132°-134° C. 1H nmr δCDCl3TMS 13.0-11.0 (brds 2H), 8.63 (s, 1 NH), 8.37-8.20, 8.05-7.90, and 7.70-7.33 (m, 4H), 5.68 (s, 1H), 5.00 (s, 2H), 3.90 (s, 6H), 3.70-2.90 (m, 4H), 2.30-1.90 (m, 4H). IR (KBr) 3650-2200, 1710, 1610, 1580, 1450, 1360, 1200, 1165 are major absorption bands.

Fuente