N-Acetylimidazolidinone → 1-{2-[(2,3-Dihydro-1H-inden-4-yl)amino]-4,5-dihydro-1H-imidazol-1-yl}ethan-1-one

HRID 2287243Notes

Reaction equation

HRID 2287243 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][NH:6][C:5]1=O)(=[O:3])[CH3:2].[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][CH2:15]2>O=P(Cl)(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][N:6]=[C:5]1[NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][CH2:15]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 79350N-AcetylimidazolidinoneHCID 1225694-Aminoindan

Product 1

HCID 30177581-{2-[(2,3-Dihydro-1H-inden-4-yl)amino]-4,5-dihydro-1H-imidazol-1-yl}ethan-1-oneYield 34.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

140.9 g (1.1 moles) of 1-acetyl-2-imidazolidinone (melting point 186°-187° C.) are introduced into 1,320 ml of POCl3 and 133.2 g (1 mole) of 4-amino-indan are added dropwise, with vigorous stirring, under conditions such that the internal temperature does not rise above 50° C. After completion of the addition, stirring is continued for 40 hours at 50° C. The excess POCl3 is then distilled off as completely as possible under reduced pressure on a rotary evaporator and the distillation residue is added to 5 l of ice water whilst keeping the temperature at ≤15° C. by further addition of ice. The pH is brought to 11 by means of 25% strength sodium hydroxide solution, whilst cooling with ice, the mixture is repeatedly extracted with chloroform, the combined chloroform phases are again washed with 1 liter of 2 N sodium hydroxide solution and are then washed neutral with water and dried over anhydrous sodium sulfate, and the chloroform is distilled off. The residue is recrystallized from isopropanol. 84.3 g of pure 1-acetyl-(4-indanylamino)-2-imidazoline of melting point 180.5°-182° C. are obtained.

Workup

  1. additionare added dropwise, with vigorous stirring, under conditions such that the internal temperature
  2. customdoes not rise above 50° C
  3. additionAfter completion of the addition
  4. distillationThe excess POCl3 is then distilled off as completely as possible under reduced pressure
  5. customon a rotary evaporator
  6. additionthe distillation residue is added to 5 l of ice water
  7. customat ≤15° C.
  8. additionby further addition of ice
  9. temperaturewhilst cooling with ice
  10. extractionthe mixture is repeatedly extracted with chloroform
  11. washthe combined chloroform phases are again washed with 1 liter of 2 N sodium hydroxide solution
  12. washare then washed neutral with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe chloroform is distilled off
  15. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-10914f72929440ecb823ba953f270a5f
Source dataset
uspto-grants-1981_05
Patent number
US04269990

Reaction notes

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