Potassium Carbonate → 2-Chloro-4-(pyrrolidin-1-ylmethyl)-thiazole

HRID 1046430Notes

Reaction equation

HRID 1046430 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]Cl)[N:6]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 109208992-Chloro-4-(chloromethyl)-1,3-thiazole

Product 1

HCID 581140122-Chloro-4-(pyrrolidin-1-ylmethyl)-thiazoleYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-4-chloromethyl-thiazole (610 mg, 3.6 mmol), pyrrolidine (0.4 mL, 4.8 mmol), and potassium carbonate (1.05 g, 7.6 mmol) were stirred in DMF (6 mL) for 5 hours. After completion, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was thrice extracted with ethyl acetate and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-5% [8:1 EtOH:NH4OH(aq)]/DCM). This resulted in 457 mg (63% yield) of the title compound as a white solid.

Workup

  1. customAfter completion, the reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-5% [8:1 EtOH:NH4OH(aq)]/DCM)

Sources & evidence

ORD record
ord-9030a0a4809f4b0b9877e571f8108c47
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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