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

HRID 19497

反応式

HRID 19497 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

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).

後処理

  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

出典と根拠

ORDレコード
ord-926a7d543911489b90421c99fc1fb825
出典データセット
uspto-grants-2010_06
特許番号
US07745437B2

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