5-[2-(4-Chloro-phenyl)-[1,3]dioxolan-2-yl]-3-(3-iodo-phenyl)-benzo[c]isoxazole → [6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methanone

HRID 1369973Notes

Reaction equation

HRID 1369973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13]3[CH:28]=[CH:27][C:16]4=[N:17][O:18][C:19]([C:20]5[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=5)=[C:15]4[CH:14]=3)OCC[O:9]2)=[CH:4][CH:3]=1>O1CCCC1.C(Cl)Cl.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:17][CH:16]1[CH:15]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([I:26])[CH:21]=2)=[O:18])[CH:14]=[C:13]([C:8](=[O:9])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:28]=[CH:27]1

Participants

5

Reactant 1

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

Product 1

HCID 15489628[6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methanoneYield 99.5%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalyst2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[2-(4-Chloro-phenyl)-[1,3]dioxolan-2-yl]-3-(3-iodo-phenyl)-benzo[c]isoxazole (65.4 g, 130 mMol) was dissolved in a solution of tetrahydrofuran (THF) (500 mL) and DCM (100 mL). To this solution, was added 500 mL of titanium(III) chloride (10 wt. % solution in 20-30 wt. % hydrochloric acid (HCl)) and the reaction mixture was stirred for 1 hour. An additional 100 mL of titanium(III) chloride (10 wt. % solution in 20-30 wt. % HCl) was added to the reaction mixture and the reaction mixture was stirred for 2.5 hours. The reaction mixture was then poured into ice water and the resulting heterogeneous solution was extracted with DCM. The DCM layer was successively washed with aqueous saturated NaHCO3 and brine. The DCM layer was dried over MgSO4, filtered and concentrated under vacuum to give titled compound as an orange oil (60 g). The oil was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 2.5 hours
  2. extractionthe resulting heterogeneous solution was extracted with DCM
  3. washThe DCM layer was successively washed with aqueous saturated NaHCO3 and brine
  4. dry with materialThe DCM layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-25eb567754304e56895139d6b4197b11
Source dataset
uspto-grants-2003_06
Patent number
US06579887B2

Reaction notes

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