Acetic Acid → HCID 233033, compound

HRID 2261112Notes

Reaction equation

HRID 2261112 reaction equation
[S:1]1CC[NH:3][CH2:2]1.[CH:6]1[C:11]([CH:12]=O)=[CH:10][C:9]2[O:14][CH2:15][O:16][C:8]=2[CH:7]=1.NC[CH2:19][C:20]([OH:22])=O.C(O)(=[O:25])C>>[O:16]1[C:8]2[CH:7]=[CH:6][C:11]([CH:12]=[C:19]3[S:1][C:2](=[O:25])[NH:3][C:20]3=[O:22])=[CH:10][C:9]=2[O:14][CH2:15]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 8438PiperonalHCID 10444Thiazolidine

Product 1

HCID 233033HCID 233033, compoundYield 84%

Conditions

Temperature
100 °C

Procedure

In a 100 ml round bottom flask were placed 20 g of thiazolidine, 15.6 g of piperonal and 7.7 g of beta-alanine in 80 ml of acetic acid. The reaction was stirred for 3 h at 100° C. and then slowly cooled to room temperature, while the desired condensation product crystallized. The crystals were filtered, washed with acetic acid (rt.) and water than recrystallized from DME (25 ml), affording 28 g (84%) of pure 5-(1,3-benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione. The corresponding potassium salt was obtained via the following route: 5-(1,3-benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione was suspended in THF, followed by the addition of 1N solution of KOH in water (1.0 eq.). A clear solution has been obtained, which upon lyophilization gave pure potassium salt of 5-(1,3-benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione.

Workup

  1. customIn a 100 ml round bottom flask were placed
  2. temperatureslowly cooled to room temperature
  3. customwhile the desired condensation product
  4. customcrystallized
  5. filtrationThe crystals were filtered
  6. washwashed with acetic acid (rt.) and water
  7. customthan recrystallized from DME (25 ml)

Sources & evidence

ORD record
ord-1bd194b2b0334c8b8ffdd7a95b9d1597
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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