HCID 12674605, compound → 1-(3-Chlorophenyl)-3-[1-(3,3-dipropylazetidin-1-yl)propan-2-yl]-4-methylimidazolidin-2-one

HRID 596464Notes

Reaction equation

HRID 596464 reaction equation
Cl[CH2:2][CH:3]([N:5]1[CH:9]([CH3:10])[CH2:8][N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]1=[O:18])[CH3:4].[CH2:19]([C:22]1([CH2:26][CH2:27][CH3:28])[CH2:25][NH:24][CH2:23]1)[CH2:20][CH3:21]>C1C=CC=CC=1>[Cl:17][C:13]1[CH:12]=[C:11]([N:7]2[CH2:8][CH:9]([CH3:10])[N:5]([CH:3]([CH3:4])[CH2:2][N:24]3[CH2:25][C:22]([CH2:26][CH2:27][CH3:28])([CH2:19][CH2:20][CH3:21])[CH2:23]3)[C:6]2=[O:18])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 12674605HCID 12674605, compoundHCID 12674606HCID 12674606, compound

Product 1

HCID 30402911-(3-Chlorophenyl)-3-[1-(3,3-dipropylazetidin-1-yl)propan-2-yl]-4-methylimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 7 g. of 3-(2-chloro-1-methylethyl)-1-(m-chlorophenyl)-4-methyl-2-imidazolidinone and 10 g. of 3,3-dipropylazetidine in 100 ml. of anhydrous benzene is heated in a bomb at 150°-160° C. for 8 hours. The solvent is evaporated under vacuum and the residue is taken up with water, alkalinized with aqueous sodium carbonate and extracted with diethyl ether. The residue obtained by evaporation of the organic layer is purified by column chromatography through silica gel, using as the eluent chloroform containing 8% of methanol. Yield 8.6 g., b.p. 220° C./0.5 mm Hg.

Workup

  1. additionA mixture of 7 g
  2. customThe solvent is evaporated under vacuum
  3. extractionextracted with diethyl ether
  4. customThe residue obtained by evaporation of the organic layer
  5. customis purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-052635ad402b40818815f6a1da4f7caa
Source dataset
uspto-grants-1977_03
Patent number
US04011238

Reaction notes

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