Sodium Iodide → HCID 14727028, compound

HRID 329414Notes

Reaction equation

HRID 329414 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.Cl[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[NH:27][C:28](=O)[S:29][CH:30]=2)=[CH:22][CH:21]=1.[CH:32](N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[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]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[N:27]=[C:28]([CH3:32])[S:29][CH:30]=4)=[CH:22][CH:21]=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 14727028HCID 14727028, 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 0.95 g (4.34 mmol) 3-piperazinyl-benzisothiazole, 1.38 g (4.34 mmol) 4-(4-(2-chloroethyl)phenyl)-thiazol-2-one hydrobromide, 1.51 ml (8.68 mmol) diisopropylethylamine, 0.92 g (8.68 mmol) sodium carbonate, 2 mg. sodium iodide, and 40 ml methylisobutylketone. The reaction was refluxed 6 days, cooled, and evaporated. The residue was chromatographed on silica gel using methylene chloride/ethyl acetate as eluent and the product fractions taken up in ether/methylene chloride and precipitated by addition of ether saturated with HCl. The precipitate was filtered and dried to give a solid, m.p. 135-140° C., 1.09 g (51%). NMR (DMSO-d6) 2.74 (s, 3H), 3.1-3.7 (m, 10H), 4.1 (d, 2h), 7.3-8.2 (m, 9H).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 6 days
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. customprecipitated by addition of ether saturated with HCl
  7. filtrationThe precipitate was filtered
  8. customdried
  9. customto give a solid, m.p. 135-140° C., 1.09 g (51%)

Sources & evidence

ORD record
ord-7109ce5602a7437593da21afdab33c72
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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