Potassium Carbonate → HCID 60070918, compound

HRID 1672534Notes

Reaction equation

HRID 1672534 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][CH: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:11])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 60070918HCID 60070918, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(trifluoromethyl)benzaldehyde (3.45 mL, 25.8 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (5.40 g, 25.8 mmol), and K2CO3 (4.28 g, 31.0 mmol) in methanol (125 mL) was heated to reflux. After 2.5 hours the volatiles were evaporated, and the residue was partitioned between diethyl ether and H2O. The aqueous phase was extracted with diethyl ether, and the combined organic extract was washed with brine, dried (Na2SO4), and concentrated in vacuo. The crude product was purified by flash chromatography (Analogix Intelliflash 280; 10% to 30% ethyl acetate/hexanes eluant; SF65-400 g column), which yielded 4.01 g (68% yield) of the title compound as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.85 (m, 4H), 2.42 (s, 3H). MS (DCI+) m/z 228 (M+H)+.

Workup

  1. temperaturewas heated to reflux
  2. customAfter 2.5 hours the volatiles were evaporated
  3. customthe residue was partitioned between diethyl ether and H2O
  4. extractionThe aqueous phase was extracted with diethyl ether
  5. extractionthe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography (Analogix Intelliflash 280

Sources & evidence

ORD record
ord-a24a50b1801745dbb17d692da36c1353
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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