1,4-Dioxane → HCID 23051822, compound

HRID 1651302Notes

Reaction equation

HRID 1651302 reaction equation
O[CH:2]([CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:3][N:4]1[CH:8]=[N:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1.O1CCOCC1.CCN(S(F)(F)[F:30])CC>O>[F:30][CH:2]([CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:3][N:4]1[CH:8]=[N:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 123472(Diethylamino)sulfur trifluoride2×HCID 23051821HCID 23051821, compound

Product 1

HCID 23051822HCID 23051822, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.1 g (4.5 mmol) of 1-[2'-hydroxy-3'-(2"-methoxyethoxy)-propyl]-3-nitro-1,2,4-triazole, 10 ml of 1,4-dioxane was added and then 1.0 g (6.2 mmol) of DAST was dropwise added. Then, the mixture was reacted for a day at room temperature with stirring. After the reaction, to the reaction solution, 2 ml of water was added to decompose excess DAST. The solution was concentrated and partitioned between chloroform and water. The chloroform phase was washed with water, dried on magnesium sulfate and filtered. The filtrate was concentrated and subjected to isolation and purification by silica gel column chromatography to give 500 mg of 1-[2'-fluoro-3'-(2"-methoxyethoxy)-propyl]-3-nitro-1,2,4-triazole.

Workup

  1. customThen, the mixture was reacted for a day at room temperature
  2. customAfter the reaction
  3. concentrationThe solution was concentrated
  4. custompartitioned between chloroform and water
  5. washThe chloroform phase was washed with water
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-1e4fda5f06094e02a40a91d7a4ef3b94
Source dataset
uspto-grants-1990_05
Patent number
US04927941

Reaction notes

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