Tributyltin Chloride → 1-Methyl-4-(tributylstannyl)-1H-imidazole

HRID 606765Notes

Reaction equation

HRID 606765 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([CH3:7])[CH:6]=1.CC[Mg+].[Br-].[Sn:12](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16]>C(Cl)Cl>[CH2:21]([Sn:12]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[N:3]=[CH:4][N:5]([CH3:7])[CH:6]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 27734634-Iodo-1-methyl-1H-imidazoleHCID 178461630HCID 178461630, compound

Product 1

HCID 219011411-Methyl-4-(tributylstannyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodo-1-methylimidazole (0.424 g, 2.04 mmol) in CH2Cl2 at rt was added EtMgBr (3.0 M in Et2O, 0.75 mL, 2.25 mmol) and the resulting solution was allowed to stir for 30 min at rt. To this solution was then added Bu3SnCl (0.60 mL, 2.21 mmol) and the mixture was stirred for another 7 h. The resulting mixture was then washed (sat. NH4C1, H2O, brine), dried (Na2SO4) and evaporated to give the title compound, which was used directly in the following step without further purification:

Workup

  1. washThe resulting mixture was then washed (sat. NH4C1, H2O, brine)
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-1f3d29f8c7894ad3968306321295ad7c
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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