Water → 2-Imidazolidinone, 4-((3-(cyclopentyloxy)-4-methoxyphenyl)methyl)-

HRID 1660518Notes

Reaction equation

HRID 1660518 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]2[CH2:15][NH:14][C:13](=[O:16])[NH:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH:23]1(Br)[CH2:27][CH2:26][CH2:25][CH2:24]1.O>CS(C)=O>[CH:23]1([O:1][C:2]2[CH:3]=[C:4]([CH2:10][CH:11]3[CH2:15][NH:14][C:13](=[O:16])[NH:12]3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 20556896HCID 20556896, compound

Product 1

HCID 30588012-Imidazolidinone, 4-((3-(cyclopentyloxy)-4-methoxyphenyl)methyl)-Yield 73.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 22.22 g (100 mmoles) of the product obtained in Example 3, step (a) in 220 ml of dimethylsulphoxide, 27 g of powdered anhydrous potassium carbonate are added and the suspension is stirred at 60° C. for 30 minutes, then 12.9 ml (120 mmoles) of cyclopentyl bromide are portionwise added during 60 minutes while the temperature is kept at 60° C. The suspension is further stirred at 60° C. for 20 hours, then cooled to 25° C. and poured into 800 ml of water. The aqueous emulsion is extracted four times with 400 ml of chloroform. The collected organic phases are washed twice with 50 ml of 1 N sodium hydroxide solution, dried over anhydrous magnesium sulphate and evaporated in vacuo. To the oily residue 200 ml of benzene are added and the evaporation is repeated. The residue is triturated with 150 ml of ether and the crystals obtained are filtered after 30 minutes and washed with 50 ml of ether to give 21.30 g (73.4%) of the title compound, m.p. 104°-107° C. After recrystallization from acetone this melting point rises to 115°-116° C. On the basis of its physical properties, this product is identical with the compound obtained in Example 2, step (d).

Workup

  1. customis kept at 60° C
  2. stirringThe suspension is further stirred at 60° C. for 20 hours
  3. temperaturecooled to 25° C.
  4. extractionThe aqueous emulsion is extracted four times with 400 ml of chloroform
  5. washThe collected organic phases are washed twice with 50 ml of 1 N sodium hydroxide solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. additionTo the oily residue 200 ml of benzene are added
  9. customthe evaporation
  10. customThe residue is triturated with 150 ml of ether
  11. customthe crystals obtained
  12. filtrationare filtered after 30 minutes
  13. washwashed with 50 ml of ether

Sources & evidence

ORD record
ord-4c825157c2754a3bbb3518b5c2523df0
Source dataset
uspto-grants-1981_12
Patent number
US04308278

Reaction notes

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