O-Xylene → HCID 15452555, compound

HRID 1873071Notes

Reaction equation

HRID 1873071 reaction equation
[C:1]1([S:7]([C:10]#[N:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=[O:14].[C:18]1([CH3:25])[C:19](C)=[CH:20]C=[CH:22][CH:23]=1>>[C:1]1([S:7]([C:10]2[CH:25]=[C:18]3[CH:23]=[CH:22][O:14][C:19]3=[CH:20][N:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 7237O-Xylene2×HCID 10928Ethyl chloroformateHCID 10313279Benzenesulfonyl cyanide

Product 1

HCID 15452555HCID 15452555, compound

Conditions

Temperature
130 °C

Procedure

Benzenesulfonyl cyanide (90.2 g, 0.540 mol) and ethyl chloroformate (29.3 g, 0.270 mol) were mixed at room temperature in xylene (125 mL) and were stirred to reflux at a temperature of 120 to 140° C. A xylene (75 mL) solution of the crude 3-methylfuran-2-carbaldehyde-N-phenylimine (28.1 g) obtained above was added dropwise over 2 hours to the mixture. After all the solution had been added, the reaction mixture was heated to reflux for 3 hours, it was then cooled to room temperature, and the solvent was distilled off to give 81.3 g of crude product. This product was purified by column chromatography on silica gel, giving 17.2 g of 5-benzenesulfonylfuro[2,3-c]pyridine.

Workup

  1. additionabove was added dropwise over 2 hours to the mixture
  2. additionAfter all the solution had been added
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 3 hours
  5. temperatureit was then cooled to room temperature
  6. distillationthe solvent was distilled off
  7. customto give 81.3 g of crude product
  8. customThis product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c0f7b7460f3e45468e325779833f5f8f
Source dataset
uspto-grants-2000_08
Patent number
US06111111

Reaction notes

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