Water → HCID 11091612, compound

HRID 1841225Notes

Reaction equation

HRID 1841225 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[I:7].[H-].[Na+].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl.O>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:18])([CH3:17])[CH3:10])[C:6]=1[I:7]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27733824,5-Diiodo-1H-imidazole

Product 1

HCID 11091612HCID 11091612, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4,5-Diiodoimidazole (prepared according to D. S. Carver, S. D. Lindell, and E. A. Saville-Stones, Tetrahedron, 1997, 53, 42, 14481-14496) (10.1 g, 31.6 mmol) was added portionwise to a room temperature suspension of sodium hydride (1.38 g, 31.6 mmol, 55% in mineral oil) in dry DMF (45 ml). The reaction mixture was stirred at room temperature for 90 min, then cooled to 0° C. and treated slowly with a solution of 2-(trimethylsilyl)-ethoxymethylchloride (6.81 ml, 34.7 mmol) in DMF (10 ml). After 2 h stirring at 0° C., the reaction mixture was poured onto a mixture of H2O (200 ml) and AcOEt (50 ml). The mixture was filtered and the mother liquor was extracted 3 times with AcOEt. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed (silica, elution with hexane/AcOEt=9:1) to provide the title compound (9.44 g, 66.4%) as a pale yellow oil. MS: m/e=450.0 (M+).

Workup

  1. additionSaville-Stones, Tetrahedron, 1997, 53, 42, 14481-14496) (10.1 g, 31.6 mmol) was added portionwise to a room temperature
  2. temperaturecooled to 0° C.
  3. stirringAfter 2 h stirring at 0° C.
  4. filtrationThe mixture was filtered
  5. extractionthe mother liquor was extracted 3 times with AcOEt
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was chromatographed
  10. wash(silica, elution with hexane/AcOEt=9:1)

Sources & evidence

ORD record
ord-e16ff1bac8d94ba088be68f282162044
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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