(Diethylamino)sulfur trifluoride → HCID 67198395, compound

HRID 1408513Notes

Reaction equation

HRID 1408513 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH2:15]O)=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(S(F)(F)[F:27])CC)C>C(Cl)Cl>[F:27][CH2:15][C:14]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:11]=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67114885HCID 67114885, compound

Product 1

HCID 67198395HCID 67198395, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Intermediate 19 (0.5 g, 1.75 mmol) was dissolved in DCM (10 ml) and reaction mixture cooled to 0° C. To this (Diethylamino)sulphur trifluoride (0.46 ml, 3.5 mmol) was added drop-wise and allowed the reaction mixture to stir at rt for 30 mins. After completion of the reaction, reaction mixture diluted with DCM and washed with water. DCM removed on rotavapour to obtain the crude. Crude was purified by column chromatography using EA and petether (7:97) as eluent to afford the title compound (0.41 g) as an yellow solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.42 (d, J 9, 2H), 7.86 (d, J 9, 2H), 6.94 (d, J 3.4, 1H), 5.42 (d, J 48.4, 2H).

Workup

  1. customreaction mixture
  2. customAfter completion of the reaction, reaction mixture
  3. washwashed with water
  4. customDCM removed on rotavapour
  5. customto obtain the crude
  6. customCrude was purified by column chromatography

Sources & evidence

ORD record
ord-6e2f41def9e7404186ea7e55f5680760
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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