Oxalic Acid → HCID 19970295, compound

HRID 974985Notes

Reaction equation

HRID 974985 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=3)[N:32]=2)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OC(C)C)(C)C.CC(C)=O.O>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]([CH2:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[C:28]2[S:29][CH:30]=[C:31]([C:33]3[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=3)[N:32]=2)[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

10

Reactant 4

HCID 971Oxalic AcidHCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 10667145HCID 10667145, compound

Product 1

HCID 19970295HCID 19970295, compoundYield 84%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

25.92 ml of ethyl acrylate, 32.98 g of potassium carbonate and 7.7 g of tetrabutylammonium bromide are added to 44.8 g of 4-{2-[N-(1-benzylpiperid-4-yl)amino]-1,3-thiazol-4-yl}benzonitrile in 900 ml of toluene, and then the reaction mixture is heated under reflux for 24 hours. The reaction mixture is cooled, then water is added and the mixture is separated after settling has taken place. The organic phase is dried over sodium sulphate and then evaporated to dryness. The oil obtained is taken up in isopropyl ether and filtered on a silica bed, entraining with isopropyl ether. The evaporation of the filtrate leads to a resin which is then salified by addition of one equivalent of oxalic acid in acetone in order to provide white crystals which melt at 225° C.; yield 84%.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe mixture is separated after settling
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customevaporated to dryness
  7. customThe oil obtained
  8. filtrationfiltered on a silica bed
  9. customThe evaporation of the filtrate
  10. customto provide white crystals which
  11. custommelt at 225° C.

Sources & evidence

ORD record
ord-01131449b9af450082b92eeb9b845600
Source dataset
uspto-grants-1997_03
Patent number
US05607952

Reaction notes

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