Potassium Carbonate → HCID 21486663, compound

HRID 1414263Notes

Reaction equation

HRID 1414263 reaction equation
[C:1]([C:9]1[CH:19]=[CH:18][C:12]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][CH2:27][N:28]([CH2:31][CH2:32]Cl)[CH2:29][CH3:30]>C(#N)C>[C:1]([C:9]1[CH:19]=[CH:18][C:12]([N:13]([CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13364Diethylaminoethyl chlorideHCID 837239HCID 837239, compound

Product 1

HCID 21486663HCID 21486663, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4'-Benzoylmethanesulfonanilide (69.5 g., 0.252 mole) is dissolved in 1.4 1. of acetonitrile and heated to reflux. Potassium carbonate (35.0 g., 0.253 mole) is added followed by dropwise addition of 2-chlorotriethylamine (34.2 g., 0.252 mole) during 15 min. The reaction mixture is refluxed for 2 hrs. and then kept at room temperature for about 16 hrs. The mixture is filtered and the filtrate concentrated under vacuum. The resulting oil is dissolved in 3N HCl, the acidic solution washed with ethyl ether, and then basified with 50% aqueous NaOH to pH 11.0. The amine which separates is extracted into ethyl ether, and the ether solution is washed first with water, then with saturated sodium chloride, and dried (MgSO4). The ether is removed under reduced pressure to give 89.2 g. (95% yield) of oil which solidifies, m.p. 74°-76°C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hrs
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. dissolutionThe resulting oil is dissolved in 3N HCl
  5. washthe acidic solution washed with ethyl ether
  6. extractionThe amine which separates is extracted into ethyl ether
  7. washthe ether solution is washed first with water
  8. dry with materialwith saturated sodium chloride, and dried (MgSO4)
  9. customThe ether is removed under reduced pressure
  10. customto give 89.2 g

Sources & evidence

ORD record
ord-3c5c4a0bb34c4dc5a03878f81fb82c70
Source dataset
uspto-grants-1977_01
Patent number
US04001229

Reaction notes

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