(Diethylamino)sulfur trifluoride → HCID 86009692, compound

HRID 2054151Notes

Reaction equation

HRID 2054151 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(S(F)(F)[F:18])CC)C>ClCCl>[Cl:1][C:2]1[C:7]([C:8]([F:18])([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 593596267003-35-0

Product 1

HCID 86009692HCID 86009692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chloro-3-pyridinyl)propan-2-ol (1 g; 5.83 mmol) in dichloromethane (10 mL) cooled to −70° C. was added diethylaminosulphur trifluoride (1.1272 g; 0.857 mL; 6.993 mmol) dropwise. On completion of the addition the reaction mixture was allowed to warm to room temperature and stir for 30 min. TLC showed starting material consumed. The reaction mixture was poured onto sodium carbonate solution and extracted with dichloromethane. The dichloromethane extracts were combined, washed with water, dried over magnesium sulphate filtered and evaporated under reduced pressure to give an oil. Yield=0.9 g. 1H NMR (360 MHz) DMSO-d6 δ: 1.83 (3H, s), 1.89 (3H, s), 7.30 (1H, dd, J 4.6 and 7.7 Hz), 8.00 (1H, dd, J 1.9 and 7.9 Hz), 8.34 (1 H, dd, J 1.9 and 4.7 Hz).

Workup

  1. additionOn completion of the addition the reaction mixture
  2. customconsumed
  3. additionThe reaction mixture was poured onto sodium carbonate solution
  4. extractionextracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give an oil

Sources & evidence

ORD record
ord-e8bdbfcfaf274c049536f04c03ad0143
Source dataset
uspto-grants-2008_02
Patent number
US07329659B2

Reaction notes

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