Bromide ion → HCID 10619179, compound

HRID 2107471Notes

Reaction equation

HRID 2107471 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.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-]>C(OCC)(=O)C.CO.CCOC(C)=O.C(#N)C>[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[N:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:10](=[O:11])[CH2:9][S:8][CH2:7]2)[CH2:24][CH2:23]1

Participants

9

Reactant 5

HCID 259Bromide ionHCID 5011QuipazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 108475053-(4-Bromobutyl)-4-thiazolidinone

Product 1

HCID 10619179HCID 10619179, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-bromobutyl)-4-thiazolidinone (4.00 g), 1-(2-quinolinyl)piperazine (3.94 g), K2CO3 (6.97 g), NaI (230 mg) and acetonitrile (150 mL) was heated at 80° C. (bath temperature) under nitrogen. After 19 hours, TLC analysis (silica gel, 13% MeOH/EtOAc) showed the absence of starting bromide and the presence of one major product, Rf =0.19. The reaction mixture was cooled to room temperature, ethyl acetate (100 mL) was added, and the mixture was filtered. The filtrate was concentrated in vacuo to a solid and triturated with EtOAc. The mixture was filtered again to remove insoluble materials and the filtrate concentrated in vacuo to 6.32 g of beige solid. Chromatography of the crude product by HPLC (Waters Prep 500, one silica gel column 8% MeOH/CH2Cl2) yielded 5.67 g of a solid, mp 105°-107° C. It was recrystallized from ethyl acetate/cyclohexane to give 3.62 g of off-white crystals, mp 106°-107.5° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated in vacuo to a solid
  4. customtriturated with EtOAc
  5. filtrationThe mixture was filtered again
  6. customto remove insoluble materials
  7. concentrationthe filtrate concentrated in vacuo to 6.32 g of beige solid

Sources & evidence

ORD record
ord-f4c475e202e5480eaa6e53851b20aa80
Source dataset
uspto-grants-1990_06
Patent number
US04933453

Reaction notes

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