Dimethylformamide → Dimethyl 5-(pyrrolidin-1-yl)isophthalate

HRID 2071134ノート

反応式

HRID 2071134 の反応式
CN(C=O)C.[NH2:6][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].I[CH2:22][CH2:23][CH2:24][CH2:25]I>CN(C)C1C=CN=CC=1.O>[N:6]1([C:7]2[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:9]([CH:8]=2)[C:17]([O:19][CH3:20])=[O:18])[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 123371,4-DiiodobutaneHCID 66831Dimethyl 5-aminoisophthalate

生成物 1

HCID 57930958Dimethyl 5-(pyrrolidin-1-yl)isophthalate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

Anhydrous DMF (3 ml) was added to a flask charged with dimethyl 5-aminoisophthalate (0.250 g, 1.2 mmol, 1 eq) and 4-dimethylaminopyridine (0.308 g, 2.52 mmol, 2.1 eq) under Ar. 1,4-diiodobutane (0.16 ml, 0.37 g, 1.20 mmol, 1 eq) was added with stirring and the solution was heated to 90° C. After heating overnight the reaction was not complete. More diiodide (0.25 ml, 1.9 mmol, 1.6 eq) was added and the reaction was heated to 100° C. After heating overnight the reaction was cooled to room temperature and poured in water. The mixture was extracted with EtOAc (×2). The combined organic extracts were washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. The residue was stirred in CH2Cl2 and filtered through cotton to remove any insoluble material. The solvent was removed in vacuo. Purification via flash chromatography yielded the crude product. The crude was triturated with hexanes and the solid was collected via filtration. 0.167 g (0.63 mmol, 53% yield) of the product was collected.

後処理

  1. temperatureAfter heating overnight the reaction
  2. temperaturethe reaction was heated to 100° C
  3. temperatureAfter heating overnight the reaction
  4. temperaturewas cooled to room temperature
  5. extractionThe mixture was extracted with EtOAc (×2)
  6. washThe combined organic extracts were washed with water (×3), brine (×1)
  7. dry with materialdried over Na2SO4
  8. filtrationThe inorganics were filtered off
  9. customthe solvent was removed in vacuo
  10. stirringThe residue was stirred in CH2Cl2
  11. filtrationfiltered through cotton
  12. customto remove any insoluble material
  13. customThe solvent was removed in vacuo
  14. customPurification via flash chromatography

出典と根拠

ORDレコード
ord-57b7e6ebdbe7470abdb4755748dbb433
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

読み込み中…