4-Iodo-1-tritylimidazole → HCID 22186071, compound

HRID 1837511Notes

Reaction equation

HRID 1837511 reaction equation
C([Mg]Br)C.I[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[N+:30]([C:33]1[CH:34]=[C:35]([CH2:39][CH:40]=[O:41])[CH:36]=[CH:37][CH:38]=1)([O-:32])=[O:31]>ClCCl>[N+:30]([C:33]1[CH:34]=[C:35]([CH2:39][CH:40]([C:6]2[N:7]=[CH:8][N:9]([C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:10]=2)[OH:41])[CH:36]=[CH:37][CH:38]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 115284082-(3-nitrophenyl)acetaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 22186071HCID 22186071, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At ambient temperature, 4.2 ml of 3M ethylmagnesium bromide are poured into 5.48 g of 4-iodo-1-trityl-1H-imidazole dissolved in 30 ml of dichloromethane. After 1 hour, 1 g of the product obtained in Step 1 is dissolved in 20 ml of dichloromethane. After hydrolysis with a saturated solution of ammonium chloride, extraction with dichloromethane, and then washing the organic phase with water, the solvent is evaporated off and the residue is purified by chromatography on silica gel, using as eluant a 98/2 dichloromethane/methanol mixture.

Workup

  1. customAfter hydrolysis
  2. extractionwith a saturated solution of ammonium chloride, extraction with dichloromethane
  3. washwashing the organic phase with water
  4. customthe solvent is evaporated off
  5. customthe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-14e96b181e8a48678ca9af38b4c0785c
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Reaction notes

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