Sodium Iodide → HCID 14726982, compound

HRID 329407Notes

Reaction equation

HRID 329407 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][S:13][CH:14]=2)=[CH:6][CH:5]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:16]1.C(=O)([O-])[O-].[Na+].[Na+].C(N(C(C)C)CC)(C)C.[I-].[Na+]>C(Cl)Cl.CC(CC(C)C)=O>[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([N:24]2[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][C:4]3[CH:9]=[CH:8][C:7]([C:10]4[N:11]=[N:12][S:13][CH:14]=4)=[CH:6][CH:5]=3)[CH2:28][CH2:29]2)=[N:16]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 14726979HCID 14726979, compound

Product 1

HCID 14726982HCID 14726982, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 0.90 g (4 mmol) 4-(4-(2-chloroethyl)phenyl)-1,2,3-thiadiazole, 0.88 g (4 mmol) N-benzisothiazolylpiperazine, 0.84 g (8 mmol) sodium carbonate, 1.39 ml (8 mmol) diisopropylethyl amine, 2 mg sodium iodide, and 40 ml methylisobutyl ketone. The reaction was refluxed 2.5 days, cooled, filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to afford an oil, which was taken up in methylene chloride and precipitated by addition of ether saturated with HCl. The solid was filtered, washed with ether, dried under nitrogen, washed with acetone, and dried to afford a white solid, m.p. 257°-259° C., 1.02 g (57.4%).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 2.5 days
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica gel
  7. customto afford an oil, which
  8. customprecipitated by addition of ether saturated with HCl
  9. filtrationThe solid was filtered
  10. washwashed with ether
  11. customdried under nitrogen
  12. washwashed with acetone
  13. customdried
  14. customto afford a white solid, m.p. 257°-259° C., 1.02 g (57.4%)

Sources & evidence

ORD record
ord-350ea942b7974addbef6c06c7a0523ce
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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