Trimethylsilyl iodide → HCID 22916379, compound

HRID 1742277Notes

Reaction equation

HRID 1742277 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][P:31]([O:36]CC)(=[O:35])[O:32]CC)[C:8]2=[O:39])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][P:31]([OH:36])(=[O:32])[OH:35])[C:8]2=[O:39])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 9959140141548-31-4

Product 1

HCID 22916379HCID 22916379, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-40 °C

Procedure

Diethyl 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanephosphonate (0.58 g) was dissolved in dry chloroform, cooled to -40° C. and to it was added trimethylsilyl iodide (1.05 g) over 2 mins under an atmosphere of nitrogen. The cooling bath was removed and the reaction mixture was stirred for 2.5 hours at room temperature then evaporated to an oil and re-evaporated from methanol, treated with excess aqueous sodium bicarbonate, evaporated to an oil and re-evaporated from methanol, water and ethanol respectively. The oil was taken up in ethanol, treated with excess aqueous sodium bicarbonate, evaporated to dryness then taken up in ethanol, filtered and the filtrate evaporated to an oil which solidified under ether. The solid was dissolved in water and passed down a Dowex 1×2-200 ion exchange resin in the formate form. Elution with aqueous formic acid gave on evaporation of the solvent 7-(3,4,5-triphenyl-2-oxo-2,3-dihydroimidazol-1-yl)heptanephosphonic acid (0.078 g, 15%) as a light brown foam.

Workup

  1. customThe cooling bath was removed
  2. customthen evaporated to an oil
  3. customre-evaporated from methanol
  4. additiontreated with excess aqueous sodium bicarbonate
  5. customevaporated to an oil
  6. customre-evaporated from methanol, water and ethanol respectively
  7. additiontreated with excess aqueous sodium bicarbonate
  8. customevaporated to dryness
  9. filtrationfiltered
  10. customthe filtrate evaporated to an oil which
  11. dissolutionThe solid was dissolved in water
  12. washElution with aqueous formic acid

Sources & evidence

ORD record
ord-d1a3885b81f84adc9fe32a93fda47a79
Source dataset
uspto-grants-1994_08
Patent number
US05338752

Reaction notes

Loading…