Bromide ion → 3-[4-[1-(2-Benzothiazolyl)-4-piperazinyl]butyl]-4-thiazolidinone

HRID 484140Notes

Reaction equation

HRID 484140 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH2:9][S:8][CH2:7]1.[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-]>C(OCC)(=O)C.CO.C(Cl)Cl.C(#N)C>[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[N:21]1[CH2:22][CH2:23][N:24]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[CH2:9][S:8][CH2:7]2)[CH2:25][CH2:26]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 5921222-Piperazin-1-yl-1,3-benzothiazoleHCID 108475053-(4-Bromobutyl)-4-thiazolidinone

Product 1

HCID 107620973-[4-[1-(2-Benzothiazolyl)-4-piperazinyl]butyl]-4-thiazolidinoneYield 86%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 3-(4-bromobutyl)-4-thiazolidinone (4.00 g), 1-(2-benzothiazolyl)piperazine (4.05 g), K2CO3 (7.01 g), NaI (250 mg) and acetonitrile (160 mL) was heated at 93° (bath temperature) under nitrogen. After 19 h, TLC analysis (silica gel, 5% methanol/methylene chloride) showed the absence of starting bromide and the presence of a major product, Rf =0.26. The reaction mixture was cooled to room temperature, ethyl acetate (100 mL) was added, and the mixture filtered. The filtrate was concentrated in vacuo to a solid which was redissolved in ethyl acetate causing a white solid to precipitate. The mixture was filtered again and the filtrate concentrated in vacuo to 6.43 g of an off-white solid. Chromatography of the crude product by HPLC (Waters Prep 500, 1 silica gel column, 5% methanol/methylene chloride) yielded 5.44 g of an off-white solid. A sample of the solid (3.08 g) was recrystallized from methylene chloride (15 mL)/hexanes (85 mL) yielding 2.28 g of a crystalline solid, mp 111°-112° C.

Workup

  1. temperaturewas heated at 93° (bath temperature) under nitrogen
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated in vacuo to a solid which
  4. dissolutionwas redissolved in ethyl acetate causing a white solid
  5. customto precipitate
  6. filtrationThe mixture was filtered again
  7. concentrationthe filtrate concentrated in vacuo to 6.43 g of an off-white solid

Sources & evidence

ORD record
ord-1c7799a32b99482bbbc290d59141000d
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

Loading…