Sodium Iodide → 4-(4-(4-(4-(3-Benzisothiazolyl)piperazinyl)butyl)phenyl)-2-aminothiazole

HRID 329413Notes

Reaction equation

HRID 329413 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]=[C:14]([NH2:17])[S:15][CH:16]=2)=[CH:8][CH:7]=1.[N:18]1([C:24]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[S:26][N:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CC(CC(C)C)=O>[S:26]1[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:24]([N:18]2[CH2:19][CH2:20][N:21]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]4[N:13]=[C:14]([NH2:17])[S:15][CH:16]=4)=[CH:8][CH:7]=3)[CH2:22][CH2:23]2)=[N:25]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 142114284-(4-(4-Chlorobutyl)phenyl)-2-aminothiazole

Product 1

HCID 147270264-(4-(4-(4-(3-Benzisothiazolyl)piperazinyl)butyl)phenyl)-2-aminothiazole

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.22 g (3.52 mmol) (4-(4-(4-chlorobutyl)phenyl)-2-aminothiazole, 0.90 g (3.52 mmol) 3-piperazinyl-benzisothiazole, 1.84 ml (10.57 mmol) diisopropylethylamine, 0.75 g (7.04 mmol) sodium carbonate, 2 mg sodium iodide, and 35 ml methylisobutylketone. The reaction mixture 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 dissolved in methylene chloride/methanol and precipitated by addition of methylene chloride saturated with HCl. The precipitate was filtered and dried to give a solid, 242 mg (13%), m.p. 258-261° C. NMR (DMSO-d6): 1.6-1.8 (m, 4H), 2.7 (t, 2H), 3.2-3.6 (m, 8H), 4.1 (m, 2H), 7.20 (s, 1H), 7.3-8.2 (m, 8H).

Workup

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction mixture was refluxed 6 days
  3. temperaturecooled
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. dissolutionthe product fractions dissolved in methylene chloride/methanol
  7. customprecipitated by addition of methylene chloride saturated with HCl
  8. filtrationThe precipitate was filtered
  9. customdried
  10. customto give a solid, 242 mg (13%), m.p. 258-261° C

Sources & evidence

ORD record
ord-7988428967ad4d00a4a0655aec2fb3be
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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