Phosphorus oxychloride → Triethyl 6-chloro-2,3,5-pyridinetricarboxylate

HRID 1733840

反応式

HRID 1733840 の反応式
O=[C:2]1[NH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=[C:3]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].P(Cl)(Cl)([Cl:25])=O>CN(C)C=O>[Cl:25][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 19958207Triethyl 1,6-dihydro-6-oxo-2,3,5-pyridinetricarboxylate

生成物 1

HCID 19958209Triethyl 6-chloro-2,3,5-pyridinetricarboxylate収率 47%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of triethyl 1,6-dihydro-6-oxo-2,3,5-pyridine-tricarboxylate (39.7 g) in 300 mL of phosphorous oxychloride and 0.5 mL dimethylformamid e is stirred at 100° C. for four hours and 15 minutes. After cooling, the excess phosphorous oxychloride is removed under vacuum. The residue is taken up in 200 mL methylene chloride and the solution poured into 500 mL of ice water and the layers are separated. The aqueous layer, made basic with concentrated ammonium hydroxide and ice, is extracted with 150 mL methylene chloride. The combined methylene chloride extracts are dried over magnesium sulfate, filtered and concentrated under vacuum, and the resulting crude product is chromatogra phed on silica using 5:1 hexanes:ethyl acetate and then 4:1 hexanes:ethyl acetate as eluants affording 26.5 g (47%) of the title product as an oil.

後処理

  1. temperatureAfter cooling
  2. customthe excess phosphorous oxychloride is removed under vacuum
  3. additionthe solution poured into 500 mL of ice water
  4. customthe layers are separated
  5. extractionis extracted with 150 mL methylene chloride
  6. dry with materialThe combined methylene chloride extracts are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-9dff64f7816a44f5823c077e952a61bb
出典データセット
uspto-grants-1996_07
特許番号
US05532207

関連ノート

読み込み中…