(Diethylamino)sulfur trifluoride → HCID 22610940, compound

HRID 840530Notes

Reaction equation

HRID 840530 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([N:8]2[C:17](=[O:18])[CH:11]3[CH2:12][CH:13](O)[CH2:14][CH2:15][N:10]3[C:9]2=[O:19])=[N:6][CH:7]=1.C(N(S(F)(F)[F:27])CC)C>O>[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([N:8]2[C:17](=[O:18])[CH:11]3[CH2:12][CH:13]([F:27])[CH2:14][CH2:15][N:10]3[C:9]2=[O:19])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22610939HCID 22610939, compound

Product 1

HCID 22610940HCID 22610940, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g of 2-(5-Chloro-3-fluoro-pyridine-2-yl)-7-hydroxi-tetrahydroimidazo-(1.5-a)-pyridine-1,3-dione (isomer B) in 80 ml dichlorromethane is treated at −55° C.-−65° C. with 1.9 ml of diethylaminosulfur trifluoride (DAST) and stirred at the same temperature for 1 hr. The vessel is then allowed to stirr at room temperature over night. The resulting brownish solution is treated with ice and water and extracted with ethyl acetate. The extracts are washed with water, dried, filtered through a small siligcagel column and evaporated to give the desired product with m.p. 154-157° C.

Workup

  1. waitto stirr at room temperature over night
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with water
  4. customdried
  5. filtrationfiltered through a small siligcagel column
  6. customevaporated

Sources & evidence

ORD record
ord-2ccf764eebc24dbaaad4cee8ff76f9f1
Source dataset
uspto-grants-2002_04
Patent number
US06369002B1

Reaction notes

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