Thiazole → HCID 68709995, compound

HRID 2097558Notes

Reaction equation

HRID 2097558 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][CH2:29][C:30](N(OC)C)=[O:31])[N:27]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH3:22])[CH3:12].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][CH2:29][C:30]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)=[O:31])[N:27]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH3:22])[CH3:12]

Participants

7

Reactant 4

HCID 9256ThiazoleHCID 25517Ammonium ChlorideHCID 866183573-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-N-methoxy-N-methylpropionamideHCID 178418339Butyllithium

Product 1

HCID 68709995HCID 68709995, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution (2 ml) of thiazole (129 mg, 1.5 mmol) in THF was cooled to −70° C., and n-butyllithium (a 2.44M hexane solution) (0.62 ml, 1.5 mmol) was added, and the resulting mixture was stirred at −70° C. for 30 minutes. A solution (4 ml) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-N-methoxy-N-methylpropionamide (500 mg, 1.4 mmol) in THF was added to the reaction mixture, followed by stirring at −70° C. for 3 hours. After heating to room temperature, a saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated salt solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5). The solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol, to thereby obtain 350 mg (yield: 66%) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-1-thiazole-2-yl-1-propanone as colorless needles.

Workup

  1. stirringby stirring at −70° C. for 3 hours
  2. temperatureAfter heating to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated salt solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-9ecb4d6a993a467fa2ac004c1b0a2b67
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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