Trimethylsilyl iodide → HCID 13228938, compound

HRID 1380545Notes

Reaction equation

HRID 1380545 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9].C[Si](I)(C)C>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:20])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 12822158HCID 12822158, compound

Product 1

HCID 13228938HCID 13228938, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (2 g) was suspended in 150 ml of acetonitrile, and 4 ml of trimethylsilyl iodide was added. The mixture was stirred in an argon stream at 90° C. for 48 hours. The reaction mixture was concentrated to dryness and the residue was shaken with 100 ml each of chloroform and water. The chloroform layer was washed with water and dried under reduced pressure. The residue was purified by column chromatography using 100 g of silica gel and recrystallization from acetone-diethyl ether to give 1.1 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless needles, m.p. 193°-195° C. (decompn.).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. stirringthe residue was shaken with 100 ml each of chloroform and water
  3. washThe chloroform layer was washed with water
  4. customdried under reduced pressure
  5. customThe residue was purified by column chromatography
  6. custom100 g of silica gel and recrystallization from acetone-diethyl ether

Sources & evidence

ORD record
ord-a73282663c824f22855f25ff4191af69
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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