Methanesulfonyl chloride → HCID 59485956, compound

HRID 1972223Notes

Reaction equation

HRID 1972223 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][N:15]([CH2:28][CH2:29][OH:30])[C:14]3=[O:31])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl.O>[CH3:34][S:35]([O:30][CH2:29][CH2:28][N:15]1[CH2:16][CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:33][CH:32]=3)=[CH:12][CH:11]=2)[C:14]1=[O:31])(=[O:37])=[O:36]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59485645HCID 59485645, compound

Product 1

HCID 59485956HCID 59485956, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-(4-chlorophenoxy)phenyl)-1-(2-hydroxyethyl)-4-(3-(trifluoromethyl)phenyl)imidazolidin-2-one (340 mg, 0.713 mmol) in DCM (3.5 mL) at 0° C. are added MsCl (111 μL, 1.43 mmol) and TEA (199 μL, 1.43 mmol). The reaction mixture is stirred at room temperature overnight before removal of the solvent. The residue is taken in H2O (40 mL) and extracted with EtOAc (3×20 mL). The combined organic layer is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography (20˜70% EtOAc/hexanes) to provide the title compound (337 mg, 85% yield) as a colorless oil-like product; HPLC-MS calculated for C25H22ClF3N2O5S (M+H+) 555.1, found 555.1.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (20˜70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8a19788079314730b0fcc7e132038644
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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