Potassium Carbonate → HCID 66696609, compound

HRID 1672552Notes

Reaction equation

HRID 1672552 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:4])#[C-:2].[F:15][C:16]([F:25])([F:24])[C:17]1[O:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:4][C:3]1[N:1]=[CH:2][O:23][C:22]=1[C:20]1[O:21][C:17]([C:16]([F:24])([F:15])[F:25])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 75376655-(trifluoromethyl)furan-2-carbaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696609HCID 66696609, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (0.893 g, 4.27 mmol), 5-(trifluoromethyl)furan-2-carbaldehyde (0.70 g, 4.3 mmol), and K2CO3 (1.18 g, 8.53 mmol) in MeOH (25 mL) was heated to reflux. After 2.5 hr the reaction mixture was cooled to ambient temperature and stirred overnight. The reaction mixture was extracted with EtOAc (2×200 mL) and washed with water (2×200 mL), then washed with brine and dried over Na2SO4, filtered, and concentrated to an orange solid. The crude product was chromatographed on silica gel (Analogix® SF25-40G column, 0%-25% EtOAc/hexanes, 30 mL/min) to yield 709 mg (77%) of the title compound as a light yellow solid. 1H NMR (300 MHz, MeOH-d4) δ 8.19 (s, 1H), 7.12 (m, 1H), 6.80 (dd, J=3.7, 0.6 1H), 2.41 (s, 3H). MS (DCI+) m/z 218 (M+H).

Workup

  1. temperaturewas heated to reflux
  2. extractionThe reaction mixture was extracted with EtOAc (2×200 mL)
  3. washwashed with water (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an orange solid
  8. customThe crude product was chromatographed on silica gel (Analogix® SF25-40G column, 0%-25% EtOAc/hexanes, 30 mL/min)

Sources & evidence

ORD record
ord-85c91dbd0fa1486d9633b3e03f36427d
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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