Sodium Iodide → 3-[4-[1-(6-Chloro-1,2-benzisothiazol-3-yl)-4-piperazinyl]butyl]-2,5,5-trimethyl-4-thiazolidinone hydrochloride

HRID 484152Notes

Reaction equation

HRID 484152 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH:7]1[CH3:14].[Cl:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:21][S:22][C:18]=2[CH:17]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[ClH:15].[Cl:15][C:16]1[CH:30]=[CH:29][C:19]2[C:20]([N:23]3[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH:7]4[CH3:14])[CH2:25][CH2:24]3)=[N:21][S:22][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 104911256-Chloro-1,2-benzisothiazol-3-yl piperazineHCID 107790943-(4-Bromobutyl)-2,5,5-trimethyl-4-thiazolidinone

Product 1

HCID 148561543-[4-[1-(6-Chloro-1,2-benzisothiazol-3-yl)-4-piperazinyl]butyl]-2,5,5-trimethyl-4-thiazolidinone hydrochlorideYield 132.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-bromobutyl)-2,5,5-trimethyl-4-thiazolidinone (3.6 g), 6-chloro-1,2-benzisothiazol-3-yl piperazine (3.7 g), K2CO3 (4.0 g) and NaI (200 mg) in CH3CN (175 ml) was heated at 80° C. for 18 hours and the product was processed in substantially the same manner as in Example 10 to afford 4.714 g of product, m.p. 204°-206° C.

Sources & evidence

ORD record
ord-83a12f3ee9ac424f8a0b897d35c7785a
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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