Potassium Carbonate → HCID 68828548, compound

HRID 1727369Notes

Reaction equation

HRID 1727369 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]([CH2:14][CH3:15])=[N:11][C:10]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[ClH:1].[ClH:1].[CH2:14]([C:12]1[S:13][C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:8]=2)=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)[N:11]=1)[CH3:15]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 229326992-(Chloromethyl)-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridine

Product 1

HCID 68828548HCID 68828548, compoundYield 85%

Procedure

To a solution of 5-(2-chloromethyl-4-pyridyl)-2-ethyl-4-(3-methylphenyl)-1,3-thiazole (0.20 g, 0.61 mmol) in pyrrolidine (0.5 mL) was stirred for 1 hour at 80° C. After cooling, to this was added an aqueous potassium carbonate solution, and extracted with ethyl acetate. The extracts were washed with brine, then, dried and concentrated. The residue was purified by alumina column chromatography (hexane-ethyl acetate=2:1). The resulting oil was made into a hydrochloride by using a solution of 4N-hydrogen chloride in ethyl acetate, and recrystallized from ethanol-isopropyl ether, to obtain a title compound (0.23 g, 85%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (hexane-ethyl acetate=2:1)
  7. customrecrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-5980c7a72ace49bd9ea4021d83b2004e
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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