Magnesium → 1-Isopropyl-5-(3'-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-one

HRID 560096Notes

Reaction equation

HRID 560096 reaction equation
C1(S([N:10]2[CH2:14][CH:13]([C:15]3[CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:22]=4)[CH:18]=[CH:19][CH:20]=3)[N:12]([CH:31]([CH3:33])[CH3:32])[C:11]2=[O:34])(=O)=O)C=CC=CC=1.[Mg]>CO>[CH:31]([N:12]1[CH:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:14][NH:10][C:11]1=[O:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 445478921-Benzenesulfonyl-3-isopropyl-4-(3'-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-one

Product 1

HCID 670009481-Isopropyl-5-(3'-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-oneYield 29.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzenesulfonyl-3-isopropyl-4-(3′-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-one (example 12, step 2, 1.386 g) and magnesium (0.541 g) were suspended in methanol (30 mL). The mixture was heated to reflux for 4 h and subsequently filtered. The filtrate was concentrated and the product was purified by column chromatography (SiO2, cyclohexane/ethyl acetate 7:3=>0:1) to give 1-isopropyl-5-(3′-methanesulfonyl-biphenyl-3-yl)-imidazolidin-2-one (0.293 g) as a colorless solid. MS: 359.1 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationsubsequently filtered
  4. concentrationThe filtrate was concentrated
  5. customthe product was purified by column chromatography (SiO2, cyclohexane/ethyl acetate 7:3=>0:1)

Sources & evidence

ORD record
ord-417d8e0812ea4c068e2fba0a488c9764
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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