N-Acetylimidazolidinone → Isaglidole

HRID 867894Notes

Reaction equation

HRID 867894 reaction equation
Cl.[NH2:2][N:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:12])[CH2:4]1.C([N:16]1[CH2:20][CH2:19][NH:18][C:17]1=O)(=O)C>O=P(Cl)(Cl)Cl>[F:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][N:3]([NH:2][C:17]1[NH:18][CH2:19][CH2:20][N:16]=1)[CH2:4]2

Participants

4

Reactant 2

HCID 79350N-AcetylimidazolidinoneHCID 21289105HCID 21289105, compound

Product 1

HCID 183683IsaglidoleYield 89.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

6.0 g (0.03 mol) of 2-amino-4-fluoro-isoindoline hydrochloride and 4.5 g (0.035 mol) of 1-acetyl-imidazolin-2-one are heated at 100° C. in 70 ml of phosphorus oxytrichloride for 4 hours. After removal of the POCl3 in vacuo, the residue is dissolved in 100 ml of ethanol and the solution is heated at the boiling point for 3 hours. The solvent is distilled off, 5N NaOH is added to the residue and the crude base is extracted with methylene chloride. Recrystallization from toluene gives 5.9 g of 4-fluoro-2-(2-imidazolin-2-ylamino)-isoindoline.

Workup

  1. customAfter removal of the POCl3 in vacuo
  2. dissolutionthe residue is dissolved in 100 ml of ethanol
  3. temperaturethe solution is heated at the boiling point for 3 hours
  4. distillationThe solvent is distilled off
  5. addition5N NaOH is added to the residue
  6. extractionthe crude base is extracted with methylene chloride
  7. customRecrystallization from toluene

Sources & evidence

ORD record
ord-568602eb0fd246169a270b3126822d14
Source dataset
uspto-grants-1988_10
Patent number
US04777181

Reaction notes

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