Sodium Iodide → HCID 10150465, compound

HRID 1762097Notes

Reaction equation

HRID 1762097 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[N:15]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([N:23]2[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[NH:9][C:8](=[O:13])[CH2:7]4)[CH2:27][CH2:28]2)=[N:15]1

Participants

6

Reactant 4

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

Product 1

HCID 10150465HCID 10150465, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with N2 inlet and condenser were added 0.62 g (3.20 mmol) 5-(2-chloroethyl)-oxindole, 0.70 g (3.20 mmol) N-(1,2-benzisothiazol-3-yl)piperazine, 0.68 g (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 l) and the product with 4% methanol in ethyl acetate (1.5 l). 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 with acetone and filtering. The title compound was obtained as a high melting, non-hygroscopic solid product, m.p. 288°-288.5° C., 0.78 g (59%).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with N2 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 l)
  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-cf8e147976c6457493a0518b5c408d79
Source dataset
uspto-grants-1989_05
Patent number
US04831031

Reaction notes

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