Phenylacetonitrile → HCID 21302343, compound

HRID 860795Notes

Reaction equation

HRID 860795 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-])=[O:20])=[CH:15][CH:14]=3)[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:22]1([CH2:28]C#N)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:13]3[CH:18]=[CH:17][C:16]4[C:15]([CH:14]=3)=[C:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:20][N:19]=4)[O:9][CH2:10][CH2:11][O:12]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 154896262-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 21302343HCID 21302343, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(4-chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane (prepared as described in WO 97/21701) (0.0373 mol) was added to a vigorously stirring mixture of benzene acetonitrile (0.041 mol) and NaOH (0.186 mol) in methanol (37.3 ml) (an exothermic effect was observed and the temperature rose to 45° C.) and the mixture was stirred vigorously for 20 h. The mixture was diluted with water and filtered off. The precipitate was washed with water and a few methanol and dried. A part (3.5 g) of the residue (10.59 g, 75%) was purified by column chromatography over silica gel (eluent: DCM). The pure fractions were collected and evaporated. The residue (2.94 g) was crystallized from DIPE, yielding 2.3 g of 5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-3-phenyl-2,1-benzisoxazole, mp. 143.4° C. (intermediate 23).

Workup

  1. customrose to 45° C.
  2. stirringwas stirred vigorously for 20 h
  3. filtrationfiltered off
  4. washThe precipitate was washed with water
  5. dry with materiala few methanol and dried
  6. customA part (3.5 g) of the residue (10.59 g, 75%) was purified by column chromatography over silica gel (eluent: DCM)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customThe residue (2.94 g) was crystallized from DIPE

Sources & evidence

ORD record
ord-a269f61b92dc4e6ba3da5103bdb5786a
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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