Реакция #4234

Уравнение реакции

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

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеVolatiles were removed under vacuum
2. 2
   ДругоеSolvent 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
   ТемператураCooling
6. 6
   Другоеscratching produced a white solid which
7. 7
   Другоеwas collected
8. 8
   Другоеdried
9. 9
   Другоеto give 488 mg, m.p. 117°-123°
10. 10
    ДругоеA 400 mg sample was crystallized from acetonitrile
11. 11
    Другоеto give 269 mg
12. 12
    Другоеabsorption bands

Методика

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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