Benzamide → N-(3-((1H-Imidazol-2-yl)amino)-4-methylphenyl)benzamide

HRID 19497

반응식

HRID 19497 반응식
C(O[CH:4](OCC)[CH2:5][N:6]=[C:7]=[NH:8])C.[C:12]([NH2:20])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS(O)(=O)=O>C(O)C>[NH:20]1[CH:12]=[CH:13][N:8]=[C:7]1[NH:6][C:5]1[CH:4]=[C:14]([NH:20][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]

참가 물질

5

반응물 3

HCID 2331BenzamideHCID 6395Methanesulfonic AcidHCID 10749464N-(2,2-diethoxyethyl)carbodiimide

생성물 1

HCID 57354987N-(3-((1H-Imidazol-2-yl)amino)-4-methylphenyl)benzamide수율 100.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 19 h
  3. concentrationThe reaction mixture was concentrated (
  4. customNo purification
  5. dissolutionThe residue was dissolved in HCl solution (6N, 30 mL)
  6. customwas neutralized with 25% NaOH solution at 0° C. to pH=6
  7. stirringThe mixture was stirred for 30 minutes
  8. extractionextracted with ethanol in CH2Cl2 (100 mL)
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customdried under vacuum
  13. customThe residue was triturated in CH2Cl2 (50 mL)
  14. filtrationThe solid was collected by filtration
  15. washwashed with CH2Cl2
  16. customdried

출처 및 근거

ORD 기록
ord-926a7d543911489b90421c99fc1fb825
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745437B2

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