1-Methylhydantoin → 3-[3-(3-methylimidazolidine-2,5-dione-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 562556Notes

Reaction equation

HRID 562556 reaction equation
[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[NH:5][C:3]1=[O:4].CC([O-])(C)C.[K+].Br[CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:27]=[C:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:25][C:24]=2[S:32]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])=[O:33])[CH:20]=[CH:21][CH:22]=1>CS(C)=O.C(Cl)Cl>[CH3:1][N:2]1[CH2:8][C:6](=[O:7])[N:5]([CH2:16][C:17]2[CH:18]=[C:19]([C:23]3[CH:27]=[C:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[S:25][C:24]=3[S:32]([NH:35][C:36]([CH3:38])([CH3:37])[CH3:39])(=[O:33])=[O:34])[CH:20]=[CH:21][CH:22]=2)[C:3]1=[O:4]

Participants

6

Reactant 3

HCID 692171-MethylhydantoinHCID 23665647Potassium tert-butoxideHCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 670039673-[3-(3-methylimidazolidine-2,5-dione-1-ylmethyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamideYield 54%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methylhydantoin (33.9 mg, 0.297 mmol) in DMSO (1 mL) and t-BuOK (46.6 mg, 0.415 mmol), that had been stirred for 40 min at ambient temperature, was added a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (87.9 mg, 0.198 mmol; see Example 1(e)) in DMSO (1 mL) dropwise. The reaction mixture was stirred for 1 h at ambient temperature and then diluted with CH2Cl2 (15 mL). The organic layer was washed with water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using EtOAc:petroleum ether (35:65) as eluent to give the sub-title compound in 54% yield as a colourless syrup (51.5 mg, 0.107 mmol).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-79c177a6e78a435cb97e1bc9b7208bb1
Source dataset
uspto-grants-2011_11
Patent number
US08067418B2

Reaction notes

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