Hydrochloric Acid → HCID 178425722, compound

HRID 873788Notes

Reaction equation

HRID 873788 reaction equation
Cl.[C:2]1([CH3:29])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH2:11][C:12]([NH:14][C:15]1[NH:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-])=O)[N:19]=1)=[O:13]>C(O)C.[Fe]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]1[N:19]=[C:15]([NH:14][C:12](=[O:13])[CH2:11][O:10][C:3]2[C:2]([CH3:29])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])[NH:16][CH:17]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178425723HCID 178425723, compound2×

Product 1

HCID 178425722HCID 178425722, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Iron powder (1.0 g) was suspended in 50% aqueous ethanol solution (100 mL), 12 mol/L hydrochloric acid (1.0 mL) was added thereto, and the mixture was stirred for 30 minutes at 70° C. To the mixture was added 2-(mesityloxy)-N-[4-(2-nitrophenyl)-1H-imidazol-2-yl]acetamide (Compound 18) (875 mg, 2.3 mmol) obtained in Example 18, and the mixture was stirred for 1 hour at 70° C. The mixture was left to cool, and then the insoluble materials were removed by filtration, and then the filtrate was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then distilled under reduced pressure. The resulting residue was separated by silica gel column (0 to 3% methanol/chloroform), and the resulting crystals were dispersed in diethyl ether, collected by filtration and dried to give 520 mg of the title compound (yield 65%) expressed by the following formula (Ex. 19).

Workup

  1. customobtained in Example 18
  2. stirringthe mixture was stirred for 1 hour at 70° C
  3. waitThe mixture was left
  4. temperatureto cool
  5. customthe insoluble materials were removed by filtration
  6. extractionthe filtrate was extracted with chloroform
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customThe resulting residue was separated by silica gel column (0 to 3% methanol/chloroform)
  10. additionthe resulting crystals were dispersed in diethyl ether
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-2340af20978d45ed9190762d5ce3b72f
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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