Bromide ion → HCID 10597030, compound

HRID 1491916Notes

Reaction equation

HRID 1491916 reaction equation
[CH3:1][C:2]1([CH3:13])[S:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][CH2:10]Br)[C:3]1=[O:12].[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Br-]>C(OCC)(=O)C.CO.CCOC(C)=O.C(#N)C>[CH3:1][C:2]1([CH3:13])[S:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][CH2:10][N:27]2[CH2:28][CH2:29][N:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:14]=3)[CH2:25][CH2:26]2)[C:3]1=[O:12]

Participants

9

Reactant 5

HCID 259Bromide ionHCID 5011QuipazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 106117723-(4-Bromobutyl)-5,5-dimethyl-4-thiazolidinone

Product 1

HCID 10597030HCID 10597030, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 5,5-dimethyl-3-(4-bromobutyl)-4-thiazolidinone (4.20 g), 1-(2-quinolinyl)piperazine (3.70 g), K2CO3 (6.55 g), NaI (200 mg) and acetonitrile (150 mL) was heated at reflux (bath temperature 95° C.) under N2 for 20 h, TLC analysis (silica gel, 10% MeOH/EtOAc) showed the absence of starting bromide and the formation of a major product, Rf =0.31. The reaction mixture was cooled to room temperature and left standing for 44 h. To this was added ethyl acetate (100 ml) and the resultant mixture was filtered, The filtrate was concentrated in vacuo to an oily solid which was redissolved in ethyl acetate (200 mL) causing a white solid to precipitate, The mixture was gravity filtered and the filtrate concentrated to an off-white solid (6.86 g). Chromatography of the crude product (Waters Prep 500, 1 silica gel column, 10% MeOH/EtOAc) yielded 4.22 g of a white solid (Rf =0.26), mp 107°-111° C. It was recrystallized from ethyl acetate/hexane (1:2) to yield 2.83 g of white crystals, mp 110.5°-111.5° C.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. waitleft
  4. filtrationthe resultant mixture was filtered
  5. concentrationThe filtrate was concentrated in vacuo to an oily solid which
  6. dissolutionwas redissolved in ethyl acetate (200 mL)
  7. customto precipitate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated to an off-white solid (6.86 g)

Sources & evidence

ORD record
ord-75113c2ca89e4e348f77a3ff5b283b5c
Source dataset
uspto-grants-1994_12
Patent number
US05371087

Reaction notes

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