Sodium Iodide → 3-(4-(1-(1,2-Benzisothiazol-3-yl)-4-piperazinyl)butyl)-5-(2,2,2-trifluoroethyl)-4-thiazolidinone hydrochloride

HRID 484148Notes

Reaction equation

HRID 484148 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[S:8][CH2:7]1.[ClH:17].[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.[K+].[K+].[Na+].[I-]>C(#N)C>[ClH:17].[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][N:6]3[C:10](=[O:11])[CH:9]([CH2:12][C:13]([F:16])([F:15])[F:14])[S:8][CH2:7]3)[CH2:31][CH2:32]2)=[N:19]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 217066033-(4-Bromobutyl)-5-(2,2,2-trifluoroethyl)-4-thiazolidinone

Product 1

HCID 148561493-(4-(1-(1,2-Benzisothiazol-3-yl)-4-piperazinyl)butyl)-5-(2,2,2-trifluoroethyl)-4-thiazolidinone hydrochlorideYield 46.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(4-bromobutyl)-5-(2,2,2-trifluoroethyl)-4-thiazolidinone (3.20 g), 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (2.81 g), K2CO3 (4.83 g) and NaI (250 mg) in acetonitrile (280 ml) was heated at 70° C. for 15 hours and the product was processed in substantially the same manner as in Example 10 to afford 2.30 g of crystals, m.p. 188°-200° C.

Sources & evidence

ORD record
ord-6c0ff3b97ed74aee983111b185f5511d
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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