Isatoic Anhydride → 2-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

HRID 1608817Notes

Reaction equation

HRID 1608817 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH2:13][CH2:14][CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1>C(O)(C)C.C(OCC)(=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:13][CH2:14][CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)=[O:4]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 3082145Isohistamine

Product 1

HCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamideYield 85.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Twenty grams (0.123 mol) of isatoic anhydride were slowly added to a cold (0° C.) solution of 13.5 g (0.122 mol) of 2-(2-aminoethyl)imidazole in 220 ml isopropanol, under nitrogen. The reaction mixture was gradually warmed to room temperature and allowed to react. When the reaction was complete, as indicated by thin layer chromatography, the solution was reduced to dryness under reduced pressure and the resultant residue was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated, the organic layer was washed with water and reduced to dryness to provide a solid. This solid was recrystallized from ethanol containing a small amount of hexane to provide 24.1 g of the desired subtitled intermediate (m.p. 180°-185° C.).

Workup

  1. customto react
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with water
  4. customto provide a solid
  5. customThis solid was recrystallized from ethanol containing a small amount of hexane

Sources & evidence

ORD record
ord-80fb02e441474e73a92b956199ece31f
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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