Diethyl Ether → 4-Iodo-1-tritylimidazole

HRID 1373676Notes

Reaction equation

HRID 1373676 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(N(CC)CC)C.[C:14]1([C:20](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C>CN(C=O)C>[I:1][C:2]1[N:3]=[CH:4][N:5]([C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178506559HCID 178506559, compound

Product 1

HCID 6182524-Iodo-1-tritylimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-iodo-1-trityl-1H-imidazole (104.1, 93%) as a white solid. MH+(437).

Workup

  1. filtrationThe solid was filtered
  2. custompumped on for several hours
  3. customto yield the crude compound
  4. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-f000d3f753a44859850e151801fb50e3
Source dataset
uspto-grants-2007_01
Patent number
US07163924B2

Reaction notes

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