反応 #47775

反応方程式

N-(2,2-diethoxyethyl)carbodiimide

benzamide

methanesulfonic acid

→

N-[3-(1H-imidazol-2-ylamino)-4-methyl-phenyl]-benzamide

収率 100.1%

溶媒

ethanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 19 h
3. 3
   濃縮The reaction mixture was concentrated (
4. 4
   その他No purification
5. 5
   workup.DISSOLUTIONThe residue was dissolved in HCl solution (6N, 30 mL)
6. 6
   その他was neutralized with 25% NaOH solution at 0° C. to pH=6
7. 7
   workup.STIRRINGThe mixture was stirred for 30 minutes
8. 8
   抽出extracted with ethanol in CH2Cl2 (100 mL)
9. 9
   乾燥The combined organic layers were dried over Na2SO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated
12. 12
    その他dried under vacuum
13. 13
    その他The residue was triturated in CH2Cl2 (50 mL)
14. 14
    ろ過The solid was collected by filtration
15. 15
    洗浄washed with CH2Cl2
16. 16
    その他dried

実験手順

A mixture of N-(2,2-diethoxyethyl)carbodiimide (10.38 g, 65.6 mmol), 3-amino-4-methyl-phenyl]-benzamide (7.42 g, 32.8 mmol), methanesulfonic acid (3.20 mL, 49.3 mmol) in ethanol (200 mL) was heated at reflux for 19 h. The reaction mixture was concentrated (No purification was pursued in this step). The residue was dissolved in HCl solution (6N, 30 mL). After stirring for overnight, the reaction mixture was neutralized with 25% NaOH solution at 0° C. to pH=6, then basified with saturated sodium carbonate solution to pH=11. The mixture was stirred for 30 minutes, and extracted with ethanol in CH2Cl2 (100 mL), then 10% ethanol in CH2Cl2 (2×100 mL). The combined organic layers were dried over Na2SO4, filtered, concentrated and dried under vacuum. The residue was triturated in CH2Cl2 (50 mL). The solid was collected by filtration and washed with CH2Cl2, dried to afford the title compound N-[3-(1H-imidazol-2-ylamino)-4-methyl-phenyl]-benzamide as a white solid (4.80 g, 50%). 1H NMR 600 MHz (DMSO-d6) δ 10.79 (s, 1H), 10.11 (s, 1H), 8.00 (d, 1H, J=2.4 Hz), 7.94 (d, 2H, J=7.2 Hz), 7.60 (s, 1H), 7.56 (t, 1H, J=7.2 Hz), 7.49 (t, 2H, J=7.2 Hz), 7.25 (dd, 1H, J=2.4, 8.4 Hz), 7.04 (d, 1H, J=7.8 Hz), 6.80 (br, s, 1H), 6.65 (br, s, 1H), 2.20 (s, 3H), MS m/z 293.4 (M+1).

出典