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

HRID 1858121Notes

Reaction equation

HRID 1858121 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 9 (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 0.1N aqueous NaOH. The DCM layer was washed successively with 0.1N 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 0.1N aqueous NaOH
  6. washThe DCM layer was washed successively with 0.1N 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-8c3594e3e1f241c7ac5675c5664f252c
Source dataset
uspto-grants-2000_11
Patent number
US06150377

Reaction notes

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