تفاعل #47775

معادلة التفاعل

N-(2,2-diethoxyethyl)carbodiimide

benzamide

methanesulfonic acid

→

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

المردود 100.1%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux for 19 h
3. 3
   تركيزThe reaction mixture was concentrated (
4. 4
   أخرىNo purification
5. 5
   workup.DISSOLUTIONThe residue was dissolved in HCl solution (6N, 30 mL)
6. 6
   أخرىwas neutralized with 25% NaOH solution at 0° C. to pH=6
7. 7
   workup.STIRRINGThe mixture was stirred for 30 minutes
8. 8
   استخلاصextracted with ethanol in CH2Cl2 (100 mL)
9. 9
   تجفيفThe combined organic layers were dried over Na2SO4
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated
12. 12
    أخرىdried under vacuum
13. 13
    أخرىThe residue was triturated in CH2Cl2 (50 mL)
14. 14
    ترشيحThe solid was collected by filtration
15. 15
    غسيلwashed with CH2Cl2
16. 16
    أخرىdried

الإجراء التجريبي

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).

المصدر