Diethyl Ether → 4-Iodo-1-tritylimidazole

HRID 353766Notes

Reaction equation

HRID 353766 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)C>CN(C=O)C>[I:1][C:2]1[N:3]=[CH:4][N:5]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1

Participants

5

Reactant 3

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

Product 1

HCID 6182524-Iodo-1-tritylimidazoleYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodoimidazole (1 eq) in DMF at room temperature was added triphenylmethyl chloride (1.2 eq). After stirring at room temperature for 24 hours, the solution was poured into ice water and left stirring for 30 minutes. The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether was added to the crude compound and the solution was filtered to yield 4-Iodo-1-trityl-1H-imidazole (92%) as a white solid. MH+(437).

Workup

  1. waitleft
  2. stirringstirring for 30 minutes
  3. filtrationThe solid was filtered
  4. custompumped on for several hours
  5. customto yield the crude compound
  6. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-7fee02ea10a1428db5c8375c78c8b71b
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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