反応 #51457

反応方程式

1,3-diaminopropane

4-(4-fluorophenoxy)benzenesulfonyl chloride

→

N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONafter the addition
2. 2
   その他partitioned between ethyl acetate and water
3. 3
   workup.ADDITIONThe resulting emulsion was cleared by addition of dichloromethane
4. 4
   その他the organic layer was separated
5. 5
   抽出The aqueous layer was extracted with dichloromethane
6. 6
   抽出the combined organic layers were extracted with 0.5 N aq. sodium bisulfate
7. 7
   抽出extracted with dichloromethane (3×100 mL)
8. 8
   乾燥The combined organic layers were dried over sodium sulfate
9. 9
   濃縮concentrated to a volume of about 50 mL
10. 10
    workup.ADDITIONAddition of hexane resulting in formation of a precipitate, which
11. 11
    ろ過was collected by filtration

実験手順

To a stirred solution of 1,3-diaminopropane (6.7 mL) in 100 mL of dichloromethane at −10° C. was slowly added over a 2 hour period a solution of 4-(4-fluorophenoxy)benzenesulfonyl chloride (5.7 g, 20 mmol) in 50 mL of dichloromethane. The reaction was stirred for 15 minutes after the addition was complete, and then partitioned between ethyl acetate and water. The resulting emulsion was cleared by addition of dichloromethane, and the organic layer was separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were extracted with 0.5 N aq. sodium bisulfate. The aqueous phase was brought to pH 8 with sodium bicarbonate and then extracted with dichloromethane (3×100 mL). The combined organic layers were dried over sodium sulfate and concentrated to a volume of about 50 mL. Addition of hexane resulting in formation of a precipitate, which was collected by filtration to provide N-(3-aminopropyl)-4-(4-fluorophenoxy)benzenesulfonamide (4.27 g) as a white solid: mp 184° C. (softens), 237° C. (melts) 1H NMR (300 MHz, DMSO-d6): δ 7.84 (d, J=9 Hz, 2H), 7.38-7.21 (m, 4H), 7.12 (d, J=9 Hz, 2H), 3.6-3.2 (br s, 3H), 2.80 (dd, J=7, 7 Hz, 2H), 2.77 (dd, J=7, 7 Hz, 2H), 1.72-1.60 (m, 2H).

出典