Potassium Carbonate → HCID 66696613, compound

HRID 1672539Notes

Reaction equation

HRID 1672539 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][N:4]=1.[N+:13]([CH:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:16])#[C-:14].C([O-])([O-])=O.[K+].[K+]>CO>[CH3:16][C:15]1[N:13]=[CH:14][O:8][C:7]=1[C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:1])([F:11])[F:12])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27777626-(Trifluoromethyl)pyridine-3-carboxaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696613HCID 66696613, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(trifluoromethyl)nicotinaldehyde (7 g, 40 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (8.41 g, 40.0 mmol) and K2CO3 (6.63 g, 48.0 mmol) were heated to reflux in methanol (200 mL) overnight. The solution was cooled and the solvents removed in vacuo. The orange semi-solid was partitioned between water and ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and the solvents removed in vacuo. The crude product was purified by column chromatography with 10% to 45% ethyl acetate/hexanes as eluent to afford 8.06 g (88% yield) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 9.01 (d, J=2.03 Hz, 1H), 8.08 (dd, J=7.97, 1.86 Hz, 1H), 7.93 (s, 1H), 7.77 (d, J=8.48 Hz, 1H), 2.51 (s, 3H,). MS (ESI+) m/z 229 (M+H)+.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvents removed in vacuo
  3. customThe orange semi-solid was partitioned between water and ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customThe crude product was purified by column chromatography with 10% to 45% ethyl acetate/hexanes as eluent

Sources & evidence

ORD record
ord-c0c4e60b21f44e6293133a8d2ca06fcf
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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