Benzoic Acid → HCID 86589683, compound

HRID 2217627Notes

Reaction equation

HRID 2217627 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[S:29]1[CH2:33][C:32](=[O:34])[NH:31][C:30]1=[O:35].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>>[CH3:8][C:6]1[CH:5]=[C:4]([CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:22]=[CH:23][C:24]([CH:27]=[C:33]4[S:29][C:30](=[O:35])[NH:31][C:32]4=[O:34])=[CH:25][CH:26]=3)=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 72556534HCID 72556534, compound

Product 1

HCID 86589683HCID 86589683, compoundYield 93%

Procedure

In a 100 mL round-bottomed flask equipped with a Dean-Stark apparatus, a mixture of 45 (1.55 g, 4.2 mmol), 2,4-thiazolidinedione (0.5 g, 4.2 mmol), benzoic acid (0.62 g, 5.0 mmol) and piperidine (0.62 mL, 6.3 mmol) was azeotroped in toluene (60 mL) for 45 min under vigorous reflux. The reaction mixture was cooled then poured over 10% citric acid (40 mL) and stirred until a bright yellow solid formed. The solid was filtered and washed with water and the wet solid was azeotroped and recrystallized from toluene to yield 1.83 g (93%) of 46. 1H NMR (400 MHz, DMSO-d6): δ 12.72 (br s, 1H), 12.57 (br s, 1H), 7.77 (s, 1H), 7.70 (s, 1H), 7.63 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 7.14 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.8 Hz, 2H), 6.92 (s, 1H), 6.69 (s, 2H), 2.16 (s, 6H).

Workup

  1. customIn a 100 mL round-bottomed flask equipped with a Dean-Stark apparatus
  2. customwas azeotroped in toluene (60 mL) for 45 min under vigorous reflux
  3. temperatureThe reaction mixture was cooled
  4. additionthen poured over 10% citric acid (40 mL)
  5. customformed
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customthe wet solid was azeotroped
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-fd8ed741b6a2443f8834a0680e83fc5b
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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