Water → HCID 66696611, compound

HRID 1672594Notes

Reaction equation

HRID 1672594 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:4])#[C-:2].[F:15][C:16]1[C:23]([F:24])=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].C([O-])([O-])=O.[K+].[K+].O>CO>[F:15][C:16]1[C:23]([F:24])=[C:22]([C:25]([F:28])([F:26])[F:27])[CH:21]=[CH:20][C:17]=1[C:18]1[O:19][CH:2]=[N:1][C:3]=1[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 50074682,3-difluoro-4-(trifluoromethyl)benzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696611HCID 66696611, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1 0.0 g, 47.8 mmol), 2,3-difluoro-4-(trifluoromethyl)benzaldehyde (9.68 g, 46.1 mmol), and K2CO3 (13.1 g, 95.0 mmol) in MeOH (240 mL) was heated to reflux. After 2 hr, the reaction mixture was cooled to ambient temperature, water (700 mL) was added, and the product was extracted with EtOAc (700 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated to an orange oil. The crude product was purified by chromatography on silica gel in five batches (Analogix® SF40-240G column, 100% CH2Cl2, 65 mL/min) to afford 7.22 g (60%) of the title compound as a light yellow liquid. 1H NMR (300 MHz, DMSO-d6) δ 8.56 (s, 1H), 7.78-7.69 (m, 1H), 7.68-7.59 (m, 1H), 2.30 (d, J=2.5, 3H). MS (DCI+) m/z 264 (M+H).

Workup

  1. temperaturewas heated to reflux
  2. extractionthe product was extracted with EtOAc (700 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to an orange oil
  7. customThe crude product was purified by chromatography on silica gel in five batches (Analogix® SF40-240G column, 100% CH2Cl2, 65 mL/min)

Sources & evidence

ORD record
ord-bc362eacbf8b4dda92053b4ffbe10594
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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