Ethanol → HCID 18707172, compound

HRID 1421994Notes

Reaction equation

HRID 1421994 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([C:24]#N)[CH:21]=[CH:20][N:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C(O)C.[OH-:29].[Na+].[OH2:31]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([C:24]([OH:31])=[O:29])[CH:21]=[CH:20][N:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 18707123HCID 18707123, compound

Product 1

HCID 18707172HCID 18707172, compound

Procedure

A mixture of 500 mg of 2-(3,4-diethoxyphenyl)-4-(4-cyano-pyridyl)thiazole, 20 ml of ethanol and 17 ml of a 4% aqueous sodium hydroxide solution was refluxed for 16 hours with heating. The reaction mixture was allowed to stand. Then, 200 ml of water was added thereto. The mixture was extracted with 80 ml of dichromethane two times. The aqueous layer was made acidic (pH=about 3) with concentrated hydrochloric acid and extracted with 150 ml of ethyl acetate three times. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from ethyl acetate to obtain 290 mg of 2-(3,4-diethoxyphenyl)-4-(4-carboxy-2-pyridyl)thiazole.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperaturewith heating
  3. extractionThe mixture was extracted with 80 ml of dichromethane two times
  4. extractionextracted with 150 ml of ethyl acetate three times
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6b6f5c20ad9140988902faa9e32347d0
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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