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

HRID 1046430ノート

反応式

HRID 1046430 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9030a0a4809f4b0b9877e571f8108c47
出典データセット
uspto-grants-2013_10
特許番号
US08569302B2

反応ノート

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