N-Acetylimidazolidinone → HCID 10107209, compound

HRID 370453Notes

Reaction equation

HRID 370453 reaction equation
Cl.[NH2:2][N:3]1[CH2:11][C:10]2[C:5](=[C:6]([Cl:13])[CH:7]=[CH:8][C:9]=2[Cl:12])[CH2:4]1.C([N:17]1[CH2:21][CH2:20][NH:19][C:18]1=O)(=O)C>P(Cl)(Cl)(Cl)=O>[Cl:13][C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[C:10]2[C:5]=1[CH2:4][N:3]([NH:2][C:18]1[NH:19][CH2:20][CH2:21][N:17]=1)[CH2:11]2

Participants

4

Reactant 2

HCID 79350N-AcetylimidazolidinoneHCID 13131609HCID 13131609, compound

Product 1

HCID 10107209HCID 10107209, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

5.9 g (0.025M) of 2-amino-4,7-dichloroisoindoline hydrochloride and 3,6 g (0.028M) of 1-acetylimidazolidin-2-one are heated to 100° C. over 2 hours in 50 ml of phosphorus oxychloride. The Cl3OP is evaporated off and the residue dissolved in 100 ml of ethanol and heated to the boiling point for 1 hour to eliminate the acetyl group. The solvent is drawn off in the vacuum, the residue picked up in water, alkalized with dilute sodium hydroxide solution, and extracted with chloroform. The chloroform is evaporated, and ethyl ether added, yielding 3.4 g of 4,7-Dichloro-2-(2-imidazolin-2-ylamino)-isoindoline as a base, which is converted with ethanolic hydrochloric acid into the hydrochloride.

Workup

  1. customThe Cl3OP is evaporated off
  2. dissolutionthe residue dissolved in 100 ml of ethanol
  3. temperatureheated to the boiling point for 1 hour
  4. extractionextracted with chloroform
  5. customThe chloroform is evaporated
  6. additionethyl ether added

Sources & evidence

ORD record
ord-055949fe29d64c3a8005bb78ad3626e4
Source dataset
uspto-grants-1985_07
Patent number
US04526897

Reaction notes

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