Sodium Carbonate → HCID 86591253, compound

HRID 584929Notes

Reaction equation

HRID 584929 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.[C:24](=[O:27])([O-])[O-:25].[Na+].[Na+].[CH:30]1[C:42]2[CH:41]([CH2:43]Cl)[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1>O1CCOCC1.O>[O:22]=[C:20]1[NH:19][C:18](=[O:23])[C:17](=[CH:16][C:13]2[CH:12]=[CH:11][C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][N:2]([CH3:1])[C:24](=[O:27])[O:25][CH2:43][CH:41]4[C:42]5[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=5[C:35]5[C:40]4=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:5]=3)=[CH:15][CH:14]=2)[S:21]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 223415429-(Chloromethyl)-9H-fluoreneHCID 73884092HCID 73884092, compound

Product 1

HCID 86591253HCID 86591253, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

500 mg (0.9 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylmethylene)thiazolidine-2,4-dione (prepared in Example 12(c)) in 12 ml of aqueous 10% sodium carbonate solution are introduced into a round-bottomed flask. At 0° C., 240 mg of 9H-fluoren-9-ylmethyl chloride in 5 ml of dioxane are added dropwise. The mixture is stirred from 0° C. to room temperature for 4 hours. The reaction medium is immersed in water and extracted with ethyl acetate, after acidification to pH 4. The organic phase is dried over magnesium sulfate, filtered and evaporated. 490 mg (100%) of the expected product are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-517fb378cb7e4965a7e22ebfb7668926
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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