반응 #4234

반응 방정식

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

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타Volatiles were removed under vacuum
2. 2
   기타Solvent 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
   온도Cooling
6. 6
   기타scratching produced a white solid which
7. 7
   기타was collected
8. 8
   기타dried
9. 9
   기타to give 488 mg, m.p. 117°-123°
10. 10
    기타A 400 mg sample was crystallized from acetonitrile
11. 11
    기타to give 269 mg
12. 12
    기타absorption bands

실험 절차

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.

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