Potassium Carbonate → HCID 66696682, compound

HRID 1672577Notes

Reaction equation

HRID 1672577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=[O:6].[N+:14]([CH:16](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:17])#[C-:15].C([O-])([O-])=O.[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:15]=[N:14][C:16]=2[CH3:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 190312873-Chloro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 66696682HCID 66696682, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 45A (2.84 g, 13.6 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.85 g, 13.6 mmol), and K2CO3 (2.26 g, 16.3 mmol) in MeOH (70 mL) was heated to reflux. After 2 hr the reaction mixture was cooled to ambient temperature, and the volatiles were evaporated at reduced pressure. The residue was partitioned between Et2O and H2O. The separated aqueous layer was extracted with Et2O, and the combined organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix® Intelliflash 280; 10% to 30% EtOAc/hexanes eluant; SF40-150 g column) yielded 3.04 g (85%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.48 (s, 1H), 7.96 (d, J=8.4, 1H), 7.87 (s, 1H), 7.78 (dd, J=8.3, 0.8, 1H), 2.43 (s, 3H). MS (DCI+) m/z 262 (M+H).

Workup

  1. customthe volatiles were evaporated at reduced pressure
  2. customThe residue was partitioned between Et2O and H2O
  3. extractionThe separated aqueous layer was extracted with Et2O
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d77e042616e425fb599eda100f9b99f
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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