Acetic Acid → HCID 86647607, compound

HRID 2041993Notes

Reaction equation

HRID 2041993 reaction equation
[C:1]([C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)=[O:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.[S:32]1[CH2:36][C:35](=[O:37])[NH:34][C:33]1=[O:38].C(O)(=O)C>CCO.C(OCC)(=O)C>[C:1]([C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH:18]=[C:36]3[S:32][C:33](=[O:38])[NH:34][C:35]3=[O:37])=[CH:20][CH:21]=2)=[O:13])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 59577216HCID 59577216, compound

Product 1

HCID 86647607HCID 86647607, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-{[3-(2-tert-butylphenoxy)azetidin-1-yl]carbonyl} benzaldehyde (480 mg, 1.42 mmol) and piperidine (70 μl, 0.71 mmol) in EtOH (15.0 mL) was added 1,3-thiazolidine-2,4-dione (200 mg, 1.70 mmol) and acetic acid (17 μl) at 80° C. After 16 h the reaction mixture was diluted with ethyl acetate, washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting mixture was washed with acetonitrile and diethyl ether to provided 5-(4-{[3-(2-tert-butylphenoxy)azetidin-1-yl]carbonyl}benzylidene)-1,3-thiazolidine-2,4-dione (308 mg, 56%) as a colorless solid.

Workup

  1. washwashed with saturated sodium chloride
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting mixture was washed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-b158536dcd3c42bb91e7dcea7c0839d4
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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