Acetic Acid → 2-Iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole

HRID 1108276Notes

Reaction equation

HRID 1108276 reaction equation
[C-]#N.[Na+].[C:4](O)(=[O:6])C.[I:8][C:9]1[N:10]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[C:12]([CH:14]=[O:15])[N:13]=1>CO.[O-2].[O-2].[Mn+4]>[I:8][C:9]1[N:10]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:11]=[C:12]([C:14]([O:6][CH3:4])=[O:15])[N:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 187846372-Iodo-4-formyl-1-triphenylmethylimidazole

Product 1

HCID 187846292-Iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazoleYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of activated manganese dioxide (5.66 g, 65 mmol), sodium cyanide (833 mg, 17 mmol), and glacial acetic acid (300 mg) in methanol (70 mL) was added 2-iodo-4-formyl-1-triphenylmethylimidazole (2.33 g, 5.0 mmol) in one portion. The mixture was stirred for 1 hour at room temperature and then filtered through Celite. The filtrate was concentrated and the residue was partitioned into methylene chloride and water. The organic phase was dried (magnesium sulfate) and concentrated in vacuo to give a white foamy solid. Purification by column chromatography using ethyl acetate:hexanes (1:2) afforded 2-iodo-4-(methoxycarbonyl)-1-triphenylmethylimidazole (2.26 g, 92%) as a white solid, mp 192-194° C. 1H NMR (CDCl3) δ 7.55 (s, 1H), 7.37-7.29 (m, 9H), 7.18-7.09 (m, 6H), 3.84 (s, 3H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was partitioned into methylene chloride and water
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give a white foamy solid
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-cf8ea541e88e4790a29872701343f54e
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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