Ethanol → HCID 15077085, compound

HRID 1651304Notes

Reaction equation

HRID 1651304 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-6278da37a74643c4ae6421f0a273baf5
Source dataset
uspto-grants-1990_05
Patent number
US04927941

Reaction notes

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