Sodium Iodide → 3-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-5-methyl-thiazolidin-4-one

HRID 484147Notes

Reaction equation

HRID 484147 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH3:12])[S:8][CH2:7]1.Cl.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[N:15]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([N:23]2[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[CH:9]([CH3:12])[S:8][CH2:7]3)[CH2:27][CH2:28]2)=[N:15]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 106822173-(4-Bromobutyl)-5-methyl-4-thiazolidinoneHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 107391723-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-5-methyl-thiazolidin-4-oneYield 58.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-bromobutyl)-5-methyl-4-thiazolidinone (4.00 g), 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (4.46 g), K2CO3 (8.00 g) and NaI (300 mg) in acetonitrile (210 ml) was heated at 40°-45° C. for 64 hours and the product was processed in substantially the same manner as in Example 10 to afford 3.64 g of crystals, m.p. 113°-115° C.

Workup

  1. temperaturewas heated at 40°-45° C. for 64 hours

Sources & evidence

ORD record
ord-c1d3ecc4d5c44879bc3259c2d9984346
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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