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

HRID 1046430노트

반응식

HRID 1046430 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9030a0a4809f4b0b9877e571f8108c47
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569302B2

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