Sodium Iodide → Ziprasidone

HRID 503818Notes

Reaction equation

HRID 503818 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[NH:9][C:8](=[O:14])[CH2:7]2.[N:15]1([C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[S:23][N:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1CCCCC1>[CH:27]1[CH:28]=[CH:29][C:24]2[S:23][N:22]=[C:21]([N:15]3[CH2:16][CH2:17][N:18]([CH2:2][CH2:3][C:4]4[CH:5]=[C:6]5[CH2:7][C:8](=[O:14])[NH:9][C:10]5=[CH:11][C:12]=4[Cl:13])[CH2:19][CH2:20]3)[C:25]=2[CH:26]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Product 1

HCID 60854ZiprasidoneYield 79.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 100 g of 5-(2-chloroethyl)-6-chlorooxindole, 95.2 g of 3-(1-piperazinyl)-1,2-benzisothiazole, 92.1 g of sodium carbonate, 6.5 g of sodium iodide, 28 g of tetrabutylammonium bromide and 1000 ml of cyclohexane was refluxed until reaction completion as shown by thin layer chromatography. The reaction mass was cooled to 30° C. and the solid was filtered. 1000 ml of water was added to the wet compound and stirred for 95 minutes. The solid was filtered and washed with 100 ml water. To the wet compound, 1000 ml methanol was added and stirred for 2.5 to 3 hours at room temperature. The compound was filtered and washed with 200 ml of methanol and dried to afford 142.6 g of the title compound.

Workup

  1. temperaturewas refluxed until reaction completion
  2. filtrationthe solid was filtered
  3. addition1000 ml of water was added to the wet compound
  4. filtrationThe solid was filtered
  5. washwashed with 100 ml water
  6. additionTo the wet compound, 1000 ml methanol was added
  7. stirringstirred for 2.5 to 3 hours at room temperature
  8. filtrationThe compound was filtered
  9. washwashed with 200 ml of methanol
  10. customdried

Sources & evidence

ORD record
ord-33d0528f1d214578b5fc1ee3ee856317
Source dataset
uspto-grants-2010_08
Patent number
US07777037B2

Reaction notes

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