Sodium Iodide → HCID 86743642, compound

HRID 329412Notes

Reaction equation

HRID 329412 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br.ClCCC1C=C[C:23]([C:26]2[NH:27][C:28](=[O:31])[S:29][CH:30]=2)=[CH:22]C=1.C(=O)([O-])[O-].[Na+].[Na+].C(N(C(C)C)CC)(C)C.[I-].[Na+]>CC(CC(C)C)=O>[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:22][CH2:23][C:26]3[NH:27][C:28](=[O:31])[S:29][CH:30]=3)[CH2:3][CH2:2]2)=[N:8]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 19872077HCID 19872077, compound

Product 1

HCID 86743642HCID 86743642, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.0 g (4.57 mmol) 3-piperazinyl-benzisothiazole, 1.46 g (4.57 mmol) 4-(4-(2-chloroethyl)phenyl)thiazol-2-one hydrobromide, 970 mg (9.13 mmol) sodium carbonate, 600 mg (4.57 mmol) diisopropylethylamine, 2 mg sodium iodide, and 35 ml methylisobutylketone. The reaction was refluxed 24 hours, cooled, and evaporated. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methylene chloride/ethyl acetate as eluent. The product fractions were dissolved in methylene chloride/ethyl acetate and precipitated with HCl gas. The precipitate was filtered to give a solid, m.p. 190° C., 455 mg (21.9%).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 24 hours
  3. temperaturecooled
  4. customevaporated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel
  9. dissolutionThe product fractions were dissolved in methylene chloride/ethyl acetate
  10. customprecipitated with HCl gas
  11. filtrationThe precipitate was filtered
  12. customto give a solid, m.p. 190° C., 455 mg (21.9%)

Sources & evidence

ORD record
ord-5b9e49387752491e9b1b262ea0aea22f
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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