Ethanol → HCID 23248654, compound

HRID 1739831Notes

Reaction equation

HRID 1739831 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:14][CH2:13][CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:22]C#N)[CH:19]=[CH:20][CH:21]=1.[OH-].[Na+].[CH2:27](O)[CH3:28]>CO>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[O:3][N:1]=[C:4]3[CH:9]=[CH:8][C:7]([C:10]4([C:28]5[CH:27]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=5)[O:14][CH2:13][CH2:12][O:11]4)=[CH:6][C:5]=23)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 73722m-ChlorophenylacetonitrileHCID 2667962-(4-Nitrophenyl)-1,3-dioxolane

Product 1

HCID 23248654HCID 23248654, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Interm. (7-a) (50 g) and then (3-chlorophenyl)acetonitrile (34.8 ml) were added to a mixture of sodium hydroxide (32.8 g) in methanol (100 ml). The mixture was stirred and refluxed till complete dissolution. The reaction was carried out twice with the same quantities. The mixtures were combined. Ice and then ethanol were added. The mixture was allowed to crystallize out. The precipitate was filtered off, washed with ethanol and dried, yielding 58 g (86%) of 3-(3-chlorophenyl)-5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-2,1-benzisoxazole (interm. 9-a).

Workup

  1. temperaturerefluxed till complete dissolution
  2. customto crystallize out
  3. filtrationThe precipitate was filtered off
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-d23e0d77e6d3456199b6482e9e3473a4
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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