Acetic Acid → HCID 58312892, compound

HRID 1043505Notes

Reaction equation

HRID 1043505 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[Br:8][C:9]1[N:14]=[C:13]([CH:15]=O)[CH:12]=[CH:11][CH:10]=1.C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[Br:8][C:9]1[N:14]=[C:13](/[CH:15]=[C:5]2/[C:4](=[O:6])[NH:3][C:2](=[O:7])[S:1]/2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 58312892HCID 58312892, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

A 40 mL round-bottomed vial was charged with thiazolidine-2,4-dione (300 mg, 2.56 mmol, 1 equiv.) and 6-bromopicolinaldehyde (477 mg, 2.56 mmol, 1 equiv.). Toluene (5 mL, 0.5 M), glacial acetic acid (22 μL, 0.38 mmol, 0.15 equiv.), and piperidine (25 μL, 0.25 mmol, 0.1 equiv.) were added and the vial was purged with argon. The mixture was shaken for 16 h at 125° C. The resulting solid was collected by filtration and then washed with acetone (3×5 mL). The solid was dried under reduced pressure to provide (Z)-5-((6-bromopyridin-2-yl)methylene)thiazolidine-2,4-dione (439 mg, 731 mg theoretical, 60%). LC-MS m/z: 286 (M+1).

Workup

  1. customthe vial was purged with argon
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with acetone (3×5 mL)
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-857e1c303615415cab9360c3f1a6ac83
Source dataset
uspto-grants-2013_10
Patent number
US08563539B2

Reaction notes

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