Ethanol → HCID 15077085, compound

HRID 1464423Notes

Reaction equation

HRID 1464423 reaction equation
O[CH:2]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].CCN(S(F)(F)[F:23])CC.C(O)C>O1CCOCC1>[F:23][CH:2]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 123472(Diethylamino)sulfur trifluoride2×HCID 232743432Nitroimidazole12hydroxy3acetylpropyl

Product 1

HCID 15077085HCID 15077085, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.93 g (17.1 mmol) of 1-(2'-hydroxy-3'-acetoxypropyl)-2-nitroimidazole in 30 ml of dry dioxane, 4.00 g of DAST was dropwise added with stirring and cooling by ice. After addition, the mixture was reacted for 5 hours at room temperature with stirring. Thereafter, to the solution, 10 ml of ethanol was added to decompose excess DAST. The solution was then concentrated and partitioned between chloroform and an aqueous solution of sodium hydrogen carbonate. The chloroform phase was dried on magnesium sulfate and filtered. The filtrate was concentrated and subjected to isolation and purification by silica gel column chromatography to give 1.15 g of 1-(2'-fluoro-3'-acetoxypropyl)-2-nitroimidazole.

Workup

  1. temperaturecooling by ice
  2. additionAfter addition
  3. customthe mixture was reacted for 5 hours at room temperature
  4. stirringwith stirring
  5. concentrationThe solution was then concentrated
  6. custompartitioned between chloroform
  7. dry with materialThe chloroform phase was dried on magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-587d4854f7824717ad7893cdb5037c79
Source dataset
uspto-grants-1994_04
Patent number
US05304654

Reaction notes

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