Phosphorus oxychloride → Ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate

HRID 395634노트

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HRID 395634 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9](=O)[O:10][C:11]=2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>N1C=CC=CC=1>[Cl:23][C:9]1[O:10][C:11]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 18174756Ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate

생성물 1

HCID 12085649Ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
125 °C

실험 절차

A mixture of ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate (12.5 g), phosphorus oxychloride (24.5 g) and pyridine (3.16 g) was heated to 120-130° C. and stirred for 45 minutes. There action mixture was poured into ice-water (200 ml) and extracted with ethyl acetate (150 ml×2). The organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (100 ml) and a saturated aqueous solution of sodium chloride (100 ml) and dried over anhydrous magnesium sulfate. The organic layer was concentrated, the residue was subjected to silica gel column chromatography, and ethyl 2-chloro-4-(5-chloro-2-thienyl)-5-oxazolebutanoate was obtained as a yellow oil (5.79 g, 48%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

후처리

  1. extractionextracted with ethyl acetate (150 ml×2)
  2. washThe organic layer was washed in sequence with a 10% aqueous solution of sodium hydrogen carbonate (100 ml)
  3. dry with materiala saturated aqueous solution of sodium chloride (100 ml) and dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-d77228ccc2bd4641b6a77b789917b137
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605629B1

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