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

HRID 747429노트

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HRID 747429 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. The reaction 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-997f39b5e4864f6c85380d19d258f9c8
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396848B1

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