Reaktion #4234

Reaktionsgleichung

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

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeVolatiles were removed under vacuum
2. 2
   SonstigeSolvent 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
   TemperaturCooling
6. 6
   Sonstigescratching produced a white solid which
7. 7
   Sonstigewas collected
8. 8
   Sonstigedried
9. 9
   Sonstigeto give 488 mg, m.p. 117°-123°
10. 10
    SonstigeA 400 mg sample was crystallized from acetonitrile
11. 11
    Sonstigeto give 269 mg
12. 12
    Sonstigeabsorption bands

Vorschrift

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.

Quelle