Acetic Acid → HCID 21320295, compound

HRID 262228Notes

Reaction equation

HRID 262228 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][S:18]([CH3:20])=[O:19])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C.C(O)(=O)C(CC(O)=O)=C.[N+:34]([O-:39])([N+]([O-])=O)=[O:35]>C(Cl)(Cl)Cl.O>[CH3:20][S:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:4]2[O:3][C:2]([N+:34]([O-:39])=[O:35])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=1)=[O:19]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 811Itaconic acidHCID 25352Nitrogen oxide (N2O4)HCID 21320299HCID 21320299, compound

Product 1

HCID 21320295HCID 21320295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The product of step A is dissolved in 100 ml. of acetic acid, 3.3 g. of itaconic acid is added followed by 2.3 g. of dinitrogen tetraoxide in 10 ml. of acetic acid (the latter being added dropwise). After two hours, the mixture is poured into water and extracted with diethyl ether. The ether extracts are washed with dilute sodium bicarbonate solution, with saturated sodium chloride solution, then dried. Evaporation provides a solid which is dissolved in chloroform and chromatographically fractionated on silica gel, eluting with chloroform-carbon tetrachloride, then chloroform. The desired product elutes slowly with chloroform. It is washed with hot hexane, then recrystallized from a hexane-chloroform mixture to provide 5-methylsulfinylmethyl-2-nitro-3-phenylbenzofuran, m.p. 161°-163° C. This is the product of Example 19.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts are washed with dilute sodium bicarbonate solution, with saturated sodium chloride solution
  3. customdried
  4. customEvaporation
  5. customprovides a solid which
  6. washeluting with chloroform-carbon tetrachloride
  7. washIt is washed with hot hexane
  8. customrecrystallized from a hexane-chloroform mixture

Sources & evidence

ORD record
ord-a9642486424a410198db5f2a950deafe
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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