Methanesulfonyl chloride → 3-(3-Iodophenyl)-1-(methylsulfonyl)imidazolidine-2,4-dione

HRID 857132Notes

Reaction equation

HRID 857132 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][NH:10][C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][N:10]([S:25]([CH3:24])(=[O:27])=[O:26])[C:9]2=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 218671043-(3-Iodophenyl)imidazolidine-2,4-dione

Product 1

HCID 218671373-(3-Iodophenyl)-1-(methylsulfonyl)imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(3-iodophenyl)imidazolidine-2,4-dione (950 mg) and N,N-diisopropylethylamine (1.1 ml) in DCM (20 ml) was treated with methanesulfonyl chloride (0.453 ml) at 20° C. After 2 h the reaction mixture was diluted with DCM and washed with aqueous 2M HCl (3×20 ml) and NaHCO3 and dried (MgSO4). The solvent was removed under reduced pressure to give the title compound (1.15 g). LCMS RT=2.91 min.

Workup

  1. washwashed with aqueous 2M HCl (3×20 ml) and NaHCO3
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d681f54b0f8140aba3b910dc501f20b4
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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