(Diethylamino)sulfur trifluoride → HCID 19996508, compound

HRID 2248449Notes

Reaction equation

HRID 2248449 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][N:6]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([CH2:16]O)=[CH:11][C:10]=2[Cl:18])[C:5](=[O:19])[CH:4]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][N:6]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([CH2:16][F:28])=[CH:11][C:10]=2[Cl:18])[C:5](=[O:19])[CH:4]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 19996519HCID 19996519, compound2×

Product 1

HCID 19996508HCID 19996508, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A dry flask was flushed with nitrogen and charged with 4-trifluoromethyl-1-(2,6-dichloro-4-hydroxymethylphenyl)-2-pyridone (Compound D) [0.73 g (2.2 mmol)] and dry dichloro-methane (15 ml). The flask was cooled to -78° C. and diethylaminosulphurtrifluoride (0.31 ml, 2.4 mmol) was added slowly dropwise. The reaction was stirred at -78° C. for 2 hours and then slowly allowed to warm up to room temperature. The reaction was slowly added to a saturated solution of sodium hydrogen carbonate (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed well with water, dried over magnesium sulphate, and evaporated in vacuo to give a yellow solid which was chromatographed on silica with 50% petrol/diethyl ether as eluent. Recrystallisation from a mixture of pentane and diethylether gave 4-trifluoromethyl-1-(2,6-dichloro-4-fluoromethylphenyl)-2-pyridone (Compound 40) (0.18 g)

Workup

  1. customA dry flask was flushed with nitrogen
  2. temperatureto warm up to room temperature
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined organic layers were washed well with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a yellow solid which
  8. customwas chromatographed on silica with 50% petrol/diethyl ether as eluent
  9. customRecrystallisation
  10. additionfrom a mixture of pentane and diethylether

Sources & evidence

ORD record
ord-5c32818debf743c4ba821a71dffb815a
Source dataset
uspto-grants-1991_08
Patent number
US05039807

Reaction notes

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