Isatoic Anhydride → HCID 20085591, compound

HRID 1608834Notes

Reaction equation

HRID 1608834 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][C:15]1[N:16]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:18][N:19]=1>C(Cl)Cl.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][C:15]1[N:16]([C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:17]=[CH:18][N:19]=1)=[O:4]

Participants

6

Reactant 2

HCID 8359Isatoic AnhydrideHCID 20085689HCID 20085689, compound

Product 1

HCID 20085591HCID 20085591, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isatoic anhydride (2.65 g; 0.0162 mol) was slowly added to a room temperature solution of 5.51 g (0.0162 mol) of 2-(aminomethyl)-1-tritylimidazole in 30 ml of methylene chloride and 65 ml of isopropanol. The reaction mixture was then allowed to react overnight. The next morning 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 then a saturated sodium chloride solution, dried over anhydrous sodium sulfate and finally reduced to dryness to provide a yellow solid. This solid was filtered through silica gel using 1000 ml of methylene chloride followed by 1000 ml of a 2% methanol in methylene chloride solution. The resulting filtrate was reduced to dryness to provide a white solid. This solid was recrystallized from a 1:1 ethyl acetate/hexanes solution to provide 5.95 g of the desired subtitled intermediate (m.p 171°-175° C.).

Workup

  1. customto react overnight
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  5. customto provide a yellow solid
  6. filtrationThis solid was filtered through silica gel using 1000 ml of methylene chloride
  7. customto provide a white solid
  8. customThis solid was recrystallized from a 1:1 ethyl acetate/hexanes solution

Sources & evidence

ORD record
ord-4e2fc17b2fcb4267af41378822a10ff2
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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