Isatoic Anhydride → 2-amino-N-(3-imidazol-1-ylpropyl)benzamide

HRID 580465Notes

Reaction equation

HRID 580465 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.[N:13]1([CH2:18][CH2:19][CH2:20][NH2:21])[CH:17]=[CH:16][N:15]=[CH:14]1>C1(C)C=CC=CC=1>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:21][CH2:20][CH2:19][CH2:18][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1)=[O:4]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 27983352-amino-N-(3-imidazol-1-ylpropyl)benzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.39 of isatoic anhydride, 2.50 g of 1H-imidazol-1-propanamine and 30 ml of toluene was heated at 90° C. for 45 minutes and cooled. The toluene layer was decanted and the residue was dissolved in methylene chloride, washed with dilute sodium hydroxide solution, water and dried over magnesium sulfate. The organic layer was concentrated to obtain the desired product, mp 107°-110° C.

Workup

  1. temperaturecooled
  2. customThe toluene layer was decanted
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with dilute sodium hydroxide solution, water
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-15711c1fa58d45dcba4e9922f5a06c38
Source dataset
uspto-grants-1988_06
Patent number
US04753944

Reaction notes

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