Potassium Carbonate → HCID 66696660, compound

HRID 1672550Notes

Reaction equation

HRID 1672550 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[O:6].[N+:11]([CH:13](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:14])#[C-:12].C([O-])([O-])=O.[K+].[K+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:12]=[N:11][C:13]=2[CH3:14])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27745743-Fluoro-4-methylbenzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696660HCID 66696660, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-fluoro-4-methylbenzaldehyde (1.38 g, 10.0 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.09 g, 10.0 mmol), and K2CO3 (1.66 g, 12.0 mmol) in 50 mL methanol was heated at reflux 3 hr, then cooled to room temperature and stirred overnight. The reaction mixture was concentrated and the residue taken up in 25 mL H2O and 25 mL Et2O. The water layer was extracted with Et2O, and the organic layers were combined, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-115 g column) with 15% EtOAc/hexanes to yield 1.56 g (82%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.45-7.30 (m, 3H), 2.36 (s, 3H), 2.27 (d, J=1.9, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux 3 hr
  3. concentrationThe reaction mixture was concentrated
  4. extractionThe water layer was extracted with Et2O
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel (Analogix® SF40-115 g column) with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-5310bf73bd8f450b87b6911603a99390
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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