Potassium Carbonate → HCID 131732634, compound

HRID 879927Notes

Reaction equation

HRID 879927 reaction equation
C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:11])(=O)=O)=CC=1.[CH2:21]([N:23]([CH2:36][CH3:37])[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([CH:34]=[O:35])[CH:28]=[CH:27]2)[CH3:22].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:36]([N:23]([CH2:21][CH3:22])[C:24]1[C:25]([F:11])=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH:30]=[C:29]([CH:34]=[O:35])[CH:28]=[CH:27]2)[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 588007N-FluorobenzenesulfonimideHCID 18627787HCID 18627787, compound

Product 1

HCID 131732634HCID 131732634, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-fluorobenzenesulfonimide (57.0 milligrams, 0.18 millimole) was added to a solution of 6-diethylamino-naphthalene-2-carboxaldehyde (1, 40.0 milligrams, 0.18 millimole) in 5 milliliters of anhydrous N,N-dimethylformamide under argon at −40° C. The mixture was allowed to warm up to room temperature slowly. After 3 hours, 10 milliliters of 10% K2CO3 aqueous solution was added and the product was extracted with ethyl acetate (3×50 milliliters). Solvent was removed by rotary evaporation and the residue was purified by chromatography (SiO2, 1:1 hexane/CH2Cl2) to give 2 as yellow needles (35.0 milligrams, 79%). Rf (silica gel, 1:1 Hex/CH2Cl2)=0.74; 1H NMR (400 MHz, CDCl3) δ 1.21 (t, J=7.0 Hz, 6 H), 3.45 (q, J=7.0 Hz, 4 H), 7.25 (t, J=8.8 Hz, 1 H), 7.65 (d, J=8.8 Hz, 1 H), 7.89 (dd, J=1.2 Hz, 8.8 Hz, 1 H), 8.00 (d, J=8.8 Hz, 1 H), 8.19 (s, 1 H), 10.06 (s, 1 H).

Workup

  1. extractionthe product was extracted with ethyl acetate (3×50 milliliters)
  2. customSolvent was removed by rotary evaporation
  3. customthe residue was purified by chromatography (SiO2, 1:1 hexane/CH2Cl2)

Sources & evidence

ORD record
ord-961d31bed0ef49ad918ee1c1b326139a
Source dataset
uspto-grants-2015_03
Patent number
US08993258B2

Reaction notes

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