Imidazole → N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

HRID 1521496Notes

Reaction equation

HRID 1521496 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([I:16])[CH:4]=1.N1C=CN=C1.[Si:22](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.CN(C=O)C>[Si:22]([O:1][CH2:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][C:6]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])=[C:5]([I:16])[CH:4]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 89814728N-(4-(hydroxymethyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

Product 1

HCID 89814652N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-(4-(hydroxymethyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide (6.4 g, 17.2 mmol) and imidazole (1.76 g, 25.8 mmol) in CH2Cl2 (100 mL) and DMF (50 mL) at 0° C. was added tert-butyldiphenylsilyl chloride (5.8 mL, 22.4 mmol). The mixture was allowed to stir at rt overnight. The mixture was diluted with CH2Cl2 (100 mL), washed with 1N HCl solution, sat. aq. NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide. It was used for next step without further purification.

Workup

  1. washwashed with 1N HCl solution, sat. aq. NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-565b67c1dd824c13a70d721317853392
Source dataset
uspto-grants-2015_07
Patent number
US09073931B2

Reaction notes

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