(Diethylamino)sulfur trifluoride → HCID 19361750, compound

HRID 376297Notes

Reaction equation

HRID 376297 reaction equation
CCN(S(F)(F)[F:7])CC.[O:10]1[CH2:14][CH2:13][O:12][CH:11]1[C:15]1[N:20]=[C:19]([CH:21](O)[CH3:22])[CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>ClCCl>[O:10]1[CH2:14][CH2:13][O:12][CH:11]1[C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH:21]([F:7])[CH3:22])[N:20]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 193617486-(1,3-Dioxolan-2-yl)-α-methyl-2-pyridinemethanol

Product 1

HCID 19361750HCID 19361750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

0.81 ml of diethylamine trifluorosulfide (6.14 mmol) is added to a solution of 0.60 g of 1-(6-[1,3]-dioxolan-2-yl-pyridin-2-yl)ethanol (3.07 mmol) in 25 ml of dichloromethane cooled to -78° C. and maintained under a nitrogen atmosphere. The mixture is stirred for 30 minutes at -78° C. and then for 2 hours at room temperature. The mixture is poured slowly into a 10% aqueous solution of sodium bicarbonate. The organic phase is dried over magnesium sulfate, filtered and the solvent is evaporated off. The title product is isolated by chromatography on a silica column (eluent: chloroform). 0.42 g of a yellow oil is obtained. Yield for the 2 stages combined: 53.4%

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. waitfor 2 hours at room temperature
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-cad4fe86429a4b439ae49ce5822b4a95
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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