Sodium Iodide → HCID 14581417, compound

HRID 1935391Notes

Reaction equation

HRID 1935391 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:2]1.[Cl:16][CH2:17][CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22]2.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[ClH:16].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:17][CH2:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23](=[O:28])[CH2:22]4)[CH2:14][CH2:15]2)=[N:2]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 145813925-(2-Chloroethyl)Oxindole

Product 1

HCID 14581417HCID 14581417, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottom flask equipped with nitrogen inlet and condenser were added 0.70 grams (3.20mmol) N-(3-benzisothiazolyl)-piperazine, 0.62 grams (3.20 mmol) 5-(2-chloroethyl)-oxindole, 0.68 grams (6.40 mmol) sodium carbonate, 2 mg sodium iodide, and 30 ml methylisobutyl ketone. The reaction was refluxed 40 hours, cooled, filtered, and evaporated. The residue was chromatographed on silica gel, eluting the byproducts with ethyl acetate (1:1) and the product with 4% methanol in ethyl acetate (1.5:1). The product fractions (Rf=0.2 in 5% methanol in ethyl acetate) were evaporated, taken up in methylene chloride, and precipitated by addition of ether saturated with HCl; the solid was filtered and washed with ether, dried, and washed with acetone. The latter was done by slurrying the solid acetone and filtering. The title compound was obtained as a high melting, non-hygroscopic solid product, m.p. 288°-288.5° C., 0.78 (59%).

Workup

  1. customTo a 125 ml round-bottom flask equipped with nitrogen inlet and condenser
  2. temperatureThe reaction was refluxed 40 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting the byproducts with ethyl acetate (1:1)
  8. customThe product fractions (Rf=0.2 in 5% methanol in ethyl acetate) were evaporated
  9. customprecipitated by addition of ether saturated with HCl
  10. filtrationthe solid was filtered
  11. washwashed with ether
  12. customdried
  13. washwashed with acetone
  14. filtrationfiltering

Sources & evidence

ORD record
ord-684871043aba4e1a933367e8ce206799
Source dataset
uspto-grants-2002_05
Patent number
US06387904B2

Reaction notes

Loading…