Reaktion #47775

Reaktionsgleichung

N-(2,2-diethoxyethyl)carbodiimide

benzamide

methanesulfonic acid

→

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

Ausbeute 100.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 19 h
3. 3
   EinengenThe reaction mixture was concentrated (
4. 4
   SonstigeNo purification
5. 5
   workup.DISSOLUTIONThe residue was dissolved in HCl solution (6N, 30 mL)
6. 6
   Sonstigewas neutralized with 25% NaOH solution at 0° C. to pH=6
7. 7
   workup.STIRRINGThe mixture was stirred for 30 minutes
8. 8
   Extraktionextracted with ethanol in CH2Cl2 (100 mL)
9. 9
   TrocknenThe combined organic layers were dried over Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated
12. 12
    Sonstigedried under vacuum
13. 13
    SonstigeThe residue was triturated in CH2Cl2 (50 mL)
14. 14
    FiltrationThe solid was collected by filtration
15. 15
    Waschenwashed with CH2Cl2
16. 16
    Sonstigedried

Vorschrift

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).

Quelle