Trityl chloride → 4-Iodo-5-methyl-1-trityl-1H-imidazole

HRID 1422339Notes

Reaction equation

HRID 1422339 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[CH3:7].C(N(CC)CC)C.[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.O1CCOCC1>[C:15]([N:5]1[C:6]([CH3:7])=[C:2]([I:1])[N:3]=[CH:4]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6103104-Iodo-5-methyl-1H-imidazole

Product 1

HCID 235114374-Iodo-5-methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a cold (0° C.) solution of 4-iodo-5-methylimidazole (5.0 g, 24.0 mmol) and triethylamine (5.0 mL, 36.0 mmol) in CH2Cl2 (100 mL) and 1,4-dioxane (50 mL) was added trityl chloride (8.0 g, 29.0 mmol). The resultant mixture was stirred for 2 hours and quenched with ice and extracted with diethyl ether. The organic extracts were washed with sat. aq. NaHCO3, dried (K2CO3) and the solvent evaporated in vacuo. The product mixture was concentrated onto silica gel and chromatographed (Silica gel, 30-50% EtOAc in hexanes) to afford the title compound as a pale yellow powder.

Workup

  1. customquenched with ice
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with sat. aq. NaHCO3
  4. dry with materialdried (K2CO3)
  5. customthe solvent evaporated in vacuo
  6. concentrationThe product mixture was concentrated onto silica gel
  7. customchromatographed (Silica gel, 30-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d934be950e9d4947b09c11efd6ba48e2
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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