Réaction #4234

Équation de réaction

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

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreVolatiles were removed under vacuum
2. 2
   AutreSolvent 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
   TempératureCooling
6. 6
   Autrescratching produced a white solid which
7. 7
   Autrewas collected
8. 8
   Autredried
9. 9
   Autreto give 488 mg, m.p. 117°-123°
10. 10
    AutreA 400 mg sample was crystallized from acetonitrile
11. 11
    Autreto give 269 mg
12. 12
    Autreabsorption bands

Mode opératoire

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.

Source