Imidazole → 4-Iodo-1-tritylimidazole

HRID 2055140Notes

Reaction equation

HRID 2055140 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.N1C=CN=C1>CN(C=O)C.C(OCC)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

7

Reactant 4

HCID 795ImidazoleHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178506559HCID 178506559, compound

Product 1

HCID 6182524-Iodo-1-tritylimidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 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-]H-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
  5. customto yield 4-iodo-1-trityl-

Sources & evidence

ORD record
ord-1f9c3062bcfd4e70aa78cb55c1bc2802
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

Loading…