Acetic Acid → HCID 21320295, compound

HRID 262225Notes

Reaction equation

HRID 262225 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([N+:12]([O-:14])=[O:13])=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1.C(O)(=[O:24])C.OO>C(Cl)(Cl)Cl>[CH3:1][S:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([N+:12]([O-:14])=[O:13])=[C:9]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]=2[CH:21]=1)=[O:24]

Participants

5

Reactant 3

HCID 176Acetic Acid3×HCID 784Hydrogen Peroxide2×HCID 21320301HCID 21320301, compound

Product 1

HCID 21320295HCID 21320295, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2.8 g. (0.009 mole) of 5-methylthiomethyl-2-nitro-3-phenylbenzofuran in 200 ml. of acetic acid is obtained by warming. The solution is cooled to 20° C., and 0.51 g. (0.0045 mole) of hydrogen peroxide in 15 ml. of acetic acid is added dropwise. After 20 hours, an additional 1.02 g. of 30 percent hydrogen peroxide in 20 ml. of acetic acid is added dropwise. After an additional 2.5 hours, the reaction is poured onto ice, the precipitate is collected by filtration and washed with water, then dissolved in a dichloromethane-diethyl ether mixture. This mixture is washed with water and saturated sodium chloride solution, then dried. Evaporation provides a solid which is dissolved in chloroform and eluted through a silica gel column with more chloroform. The desired product is eluted from the silica gel with ethyl acetate, recrystallized from a benzene-hexane mixture then from aqueous ethanol to provide yellow plates of 5-methylsulfinylmethyl-2-nitro-3-phenylbenzofuran, m.p. 162°-165° C.

Workup

  1. temperatureby warming
  2. waitAfter an additional 2.5 hours
  3. additionthe reaction is poured onto ice
  4. filtrationthe precipitate is collected by filtration
  5. washwashed with water
  6. dissolutiondissolved in a dichloromethane-diethyl ether mixture
  7. washThis mixture is washed with water and saturated sodium chloride solution
  8. customdried
  9. customEvaporation
  10. customprovides a solid which
  11. washeluted through a silica gel column with more chloroform
  12. washThe desired product is eluted from the silica gel with ethyl acetate
  13. customrecrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-88011decf90344b98edcf07a677ac9ae
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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