Diethylamine → HCID 18375435, compound

HRID 2210472Notes

Reaction equation

HRID 2210472 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([S:10](F)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>O1CCCC1>[C:1]([C:4]1[CH:5]=[C:6]([S:10]([N:16]([CH2:17][CH3:18])[CH2:14][CH3:15])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8021Diethylamine2×HCID 12821Acetylbenzenesulfonyl fluoride

Product 1

HCID 18375435HCID 18375435, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 40.4 g (0.20 mol) of 3-acetylbenzenesulfonyl fluoride, 32.2 g (0.44 mol) of diethylamine in 200 ml of dry tetrahydrofuran is stirred overnight at 23° C. and then refluxed for two days. Diethylamine (10 ml) is added and the solution refluxed for 24 hours and the solvent removed. The residue is dissolved in CH2Cl2 and the solution washed with 1NHCl and H2O. The CH2Cl2 layer is dried (MgSO4) and the solvent removed to give 45 g (88%) of thick oil. A sample is chromatographed (silica gel column) with CH2Cl2 to give a viscous oil.

Workup

  1. temperaturerefluxed for two days
  2. temperaturethe solution refluxed for 24 hours
  3. customthe solvent removed
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. washthe solution washed with 1NHCl and H2O
  6. dry with materialThe CH2Cl2 layer is dried (MgSO4)
  7. customthe solvent removed

Sources & evidence

ORD record
ord-287428a4a8c94203ac242af02f0549f7
Source dataset
uspto-grants-1995_10
Patent number
US05459131

Reaction notes

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