Sodium Carbonate → HCID 19872076, compound

HRID 329419Notes

Reaction equation

HRID 329419 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:14](=[O:17])[S:15][CH:16]=2)=[CH:8][CH:7]=1.[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:19]1.C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].CC(CC(C)C)=O>[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27]2[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]4[NH:13][C:14](=[O:17])[S:15][CH:16]=4)=[CH:8][CH:7]=3)[CH2:31][CH2:32]2)=[N:19]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 19872075HCID 19872075, compound

Product 1

HCID 19872076HCID 19872076, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a 125 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.10 g (4.11 mmol) 4-(4-(4-chlorobutyl)phenyl)-thiazol-2-one, 0.90 g (4.11 mmol) N-(3-benzoisothiazolyl)piperazine, 0.87 g (8.22 mmol) sodium carbonate, 2 mg sodium iodide, and 40 ml methylisobutylketone. The reaction mixture was heated at reflux for 44 hours, cooled, filtered, and the filtrate was evaporated. The residue was chromatographed on silica gel using ethyl acetate as eluent, and the product fractions collected and evaporated. The residue was taken up in methylene chloride/methanol, treated with ether saturated with HCl, and evaporated. The resulting solid was triturated with acetone to afford 1.10 g (55%) of white solid, m.p. 140-145° C. NMR (DMSO-d6): 1.6-1.8 (m, 4H), 2.62 (t, 2H), 3.1-3.3 (m, 4H), 3.4-3.6 (m, 4H), 4.0-4.1 (m, 2H), 6.75 (d, 1H), 7.2-8.1 (m, 8H).

Workup

  1. customTo a 125 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 44 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe residue was chromatographed on silica gel
  8. customthe product fractions collected
  9. customevaporated
  10. additiontreated with ether saturated with HCl
  11. customevaporated
  12. customThe resulting solid was triturated with acetone

Sources & evidence

ORD record
ord-0a53912d954b4f368469d5efac737424
Source dataset
uspto-grants-1990_01
Patent number
US04891375

Reaction notes

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