Water → HCID 21330914, compound

HRID 1391325Notes

Reaction equation

HRID 1391325 reaction equation
I[C:2]1[O:3][C:4]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:18]([O-:23])([N+]([O-])=O)=[O:19].O>C(O)(=O)C>[CH3:17][C:16]1[C:4]2[O:3][C:2]([N+:18]([O-:23])=[O:19])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25352Nitrogen oxide (N2O4)HCID 21330920HCID 21330920, compound

Product 1

HCID 21330914HCID 21330914, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 5.0 g (0.015 mole) of 2-iodo-7-methyl-3-phenylbenzofuran from Example 9 in 100 ml of acetic acid is added dropwise 2.0 g (0.022 mole) of dinitrogen tetroxide in 10 ml of acetic acid. After stirring one hour the mixture is poured into cold water, then extracted with diethyl ether. The ether extracts are washed with water, 10% sodium bisulfite solution, water and saturated sodium chloride solution and dried. Concentration gives a tan powder which is recrystallized from aqueous ethanol to give yellow crystals of 7-methyl-2-nitro-3-phenylbenzofuran, m.p. 123°-126° C. This product is identical to the product of Example 2 according to comparative infrared spectral analysis.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts are washed with water, 10% sodium bisulfite solution, water and saturated sodium chloride solution
  3. customdried
  4. concentrationConcentration
  5. customgives a tan powder which
  6. customis recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-627921df600f47b5854b33b94bd24b37
Source dataset
uspto-grants-1979_02
Patent number
US04141990

Reaction notes

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