(Diethylamino)sulfur trifluoride → HCID 13616595, compound

HRID 510786Notes

Reaction equation

HRID 510786 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9](O[Si](C)(C)C)[C:10]#[N:11].C(N(S(F)(F)[F:23])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([F:23])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11403074HCID 11403074, compound

Product 1

HCID 13616595HCID 13616595, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(2,4-dichlorophenyl)-2-(trimethylsilyloxy)acetonitrile (1.57 g, 5.73 mmol) in dichloromethane (20 ml) under argon at −78° C. was added (diethylamino)sulfur trifluoride (1.51 ml, 11.5 mmol) dropwise over 15 minutes. The reaction was stirred at this temperature for 20 minutes, then warmed to 0° C. and allowed to stir for an additional 30 minutes. The reaction was poured onto a mixture of ice water and saturated sodium bicarbonate and allowed to stir for 30 minutes. The mixture was extracted with ether twice, and the combined organic layers were washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 1.05 g of the title compound (89% yield).

Workup

  1. stirringto stir for an additional 30 minutes
  2. stirringto stir for 30 minutes
  3. extractionThe mixture was extracted with ether twice
  4. washthe combined organic layers were washed with saturated sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-19a80653a53147f892a54aad6b90b980
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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