Sodium Hydroxide → 5-[2-(4-Chloro-phenyl)-[1,3]dioxolan-2-yl]-3-(3-iodo-phenyl)-benzo[c]isoxazole

HRID 479571Notes

Reaction equation

HRID 479571 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=O)=[CH:15][CH:14]=3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[I:22][C:23]1[CH:24]=[C:25]([CH2:29]C#N)[CH:26]=[CH:27][CH:28]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]3[CH:14]=[CH:15][C:16]4=[N:19][O:21][C:29]([C:25]5[CH:26]=[CH:27][CH:28]=[C:23]([I:22])[CH:24]=5)=[C:17]4[CH:18]=3)[O:9][CH2:10][CH2:11][O:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27593682-(3-Iodophenyl)acetonitrileHCID 154896262-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 154896275-[2-(4-Chloro-phenyl)-[1,3]dioxolan-2-yl]-3-(3-iodo-phenyl)-benzo[c]isoxazoleYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane (38.7 g, 127 mMol) was suspended in 190 mL of methanol (MeOH) under an atmosphere of dry N2. To this solution was added (3-iodophenyl)acetonitrile (46.3 g, 190 mMol) and 25.4 g (625 mMol) of sodium hydroxide (NaOH). The solution was then heated to reflux and reacted at this temperature for 2 hours. The reaction mixture was cooled to ambient temperature and the MeOH was removed under vacuum. The resulting red oil was partitioned between dichloromethane (DCM) and 0.1 N aqueous NaOH. The DCM layer was washed successively with 0.1 N aqueous NaOH and then brine. The DCM layer was dried over MgSO4, filtered and concentrated under vacuum to give a dark red oil. The oil was stirred in MeOH and the titled compound precipitated out as a yellow solid. The yellow solid was washed with MeOH and dried under vacuum to give 52.4 g of the titled compound which was used without further purification.

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux
  3. customreacted at this temperature for 2 hours
  4. customthe MeOH was removed under vacuum
  5. customThe resulting red oil was partitioned between dichloromethane (DCM) and 0.1 N aqueous NaOH
  6. washThe DCM layer was washed successively with 0.1 N aqueous NaOH
  7. dry with materialThe DCM layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto give a dark red oil
  11. customthe titled compound precipitated out as a yellow solid
  12. washThe yellow solid was washed with MeOH
  13. customdried under vacuum

Sources & evidence

ORD record
ord-69285dee76284a1da39a0d4bdbd6b202
Source dataset
uspto-grants-2003_11
Patent number
US06645982B2

Reaction notes

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