Sodium Iodide → HCID 14727018, compound

HRID 329409Notes

Reaction equation

HRID 329409 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[N:14][S:15][CH:16]=2)=[CH:8][CH:7]=1.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:18]1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(OCC)(=O)C.CC(CC(C)C)=O>[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([N:26]2[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]4[N:13]=[N:14][S:15][CH:16]=4)=[CH:8][CH:7]=3)[CH2:30][CH2:31]2)=[N:18]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 19872068HCID 19872068, compound

Product 1

HCID 14727018HCID 14727018, compound

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 65 ml round-bottom flask equipped with condenser and N2 inlet were added 1.43 g (5.66 mmol) 4-(4-(4-chlorobutyl)phenyl)-1,2,3-thiadiazole, 0.90 g (4.11 mmol) N-benzisothiazolylpiperazine, 1.43 ml (8.22 mmol)diisopropylethyl amine, 0.87 g (8.22 mmol) sodium carbonate, 2 mg sodium iodide, and 30 ml methylisobutyl ketone. The reaction was refluxed for 24 hours, cooled, filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to give an oil, which was taken up in ethyl acetate and precipitated by addition of ethyl acetate saturated with HCl. The solid was filtered, washed with ethyl acetate, and dried to afford 1.70 g (87.6%), m.p. 246°-247° C., white solid.

Workup

  1. customTo a 65 ml round-bottom flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica gel
  7. customto give an oil, which
  8. customprecipitated by addition of ethyl acetate saturated with HCl
  9. filtrationThe solid was filtered
  10. washwashed with ethyl acetate
  11. customdried
  12. customto afford 1.70 g (87.6%), m.p. 246°-247° C., white solid

Sources & evidence

ORD record
ord-e8b3066c1cf1453fb3130675194718b1
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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