Methanesulfonyl chloride → HCID 57976191, compound

HRID 1865321Notes

Reaction equation

HRID 1865321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([CH2:15][OH:16])([CH3:14])[NH:10][C:9]2=[O:17])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([CH2:15][O:16][S:23]([CH3:22])(=[O:25])=[O:24])([CH3:14])[NH:10][C:9]2=[O:17])=[CH:4][C:3]=1[C:18]([F:19])([F:21])[F:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57976187HCID 57976187, compound

Product 1

HCID 57976191HCID 57976191, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Chloro-3-trifluoromethyl-phenyl)-5-hydroxymethyl-5-methyl-imidazolidine-2,4-dione from Example 10 (1.01 g, 3.14 mmoL) in DCM (10 mL) was treated with TEA (0.66 mL, 4.70 mmoL) followed by MsCl (360 mg, 3.14 mmoL) at 0° C. The reaction was slowly warmed to room temperature and stirring for another 2 hrs. The crude product was partitioned between DCM and water. The organic layer was washed with sat. NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated, then purified by silica gel column chromatography using heptane and ethyl acetate as eluent to afford the title compound as a white solid (1.05 g, yield 85%).

Workup

  1. customThe crude product was partitioned between DCM and water
  2. washThe organic layer was washed with sat. NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-10db6f45806c4599b6895a06267cfdbc
Source dataset
uspto-grants-2009_12
Patent number
US07626036B2

Reaction notes

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