Hydrochloric Acid → HCID 21568993, compound

HRID 1579614Notes

Reaction equation

HRID 1579614 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](N)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.N([O-])=O.[Na+].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([CH3:24])=[O:23]>O.C(#N)C.CCOCC>[CH3:24][C:22]([C:18]1[O:17][C:21]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:20][CH:19]=1)=[O:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 145052-AcetylfuranHCID 796174-(Methylsulfonyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 21568993HCID 21568993, compoundYield 9.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 200 g (1.16 mole) of p-aminophenyl methyl sulfone, 405 ml of concentrated hydrochloric acid, and 150 ml of water was heated at 80° for 20 minutes and then cooled to 0°. A solution of 80 g (1.16 mole) of sodium nitrite in 270 ml of water was added dropwise while maintaining the temperature between 0°-5° by means of an ice bath. The near solution was kept at 0° for 15 minutes. A solution of 129 g (1.16 mole) of methyl 2-furyl ketone in 125 ml of acetonitrile was added followed by a solution of 30 g of CuCl2 .2H2O in 100 ml of water. The reaction, after stirring in the cold for one hour, was allowed to warm to room temperature at which time it became exothermic and was controlled below 55° by means of an ice bath. The reaction, after stirring overnight at room temperature, was treated with 500 ml of ether with a solid forming. The solid was filtered, washed with dilute NaOH solution, and refluxed in acetonitrile with the insoluble material being removed by filtration. The filtrate was again heated to reflux and water was added to the "cloud point". Upon cooling an oil formed from which the acetonitrile was decanted. The acetonitrile was again treated with water and the resulting solid was filtered and recrystallized from ethyl acetate/charcoal and airdried to yield 28 g (9%) of 5-(p-methylsulfonylphenyl)-2-furyl methyl ketone. An analytical sample was prepared by drying a sample in the vacuum pistol at the temperature of refluxing CHCl3, m.p. 160°-164°.

Workup

  1. temperaturewas heated at 80° for 20 minutes
  2. temperaturecooled to 0°
  3. temperaturewhile maintaining the temperature between 0°-5° by means of an ice bath
  4. customThe reaction
  5. customwas controlled below 55° by means of an ice bath
  6. customThe reaction
  7. stirringafter stirring overnight at room temperature
  8. customforming
  9. filtrationThe solid was filtered
  10. washwashed with dilute NaOH solution
  11. temperaturerefluxed in acetonitrile with the insoluble material
  12. custombeing removed by filtration
  13. temperatureThe filtrate was again heated
  14. temperatureto reflux
  15. additionwater was added to the "cloud point"
  16. temperatureUpon cooling an oil
  17. customformed from which the acetonitrile
  18. customwas decanted
  19. additionThe acetonitrile was again treated with water
  20. filtrationthe resulting solid was filtered
  21. customrecrystallized from ethyl acetate/charcoal

Sources & evidence

ORD record
ord-2a67a12513b9495f8cd7343b665f1d3b
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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