Methyl 4-(p-chlorophenoxy)butyrate → HCID 178508402, 화합물

HRID 1752810

반응식

HRID 1752810 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10](OC)=O)=[CH:4][CH:3]=1.C(=O)(O)O.[NH2:20][NH:21][C:22]([NH2:24])=[NH:23]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]2[N:23]=[C:22]([NH2:24])[NH:21][N:20]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 547990Methyl 4-(p-chlorophenoxy)butyrateHCID 178513185HCID 178513185, 화합물2회

생성물 1

HCID 178508402HCID 178508402, 화합물수율 72.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
125 °C

실험 절차

A mixture of methyl 4-(4-chlorophenoxy)butanoate (1.4 g, 6.13 mmol), aminoguanidine bicarbonate (2.08 g, 15.3 mmol), and pyridine (12 mL) was added to a 100 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and heated to 125° C. using an oil bath. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 nm. The mixture was heated for 20 hours, and an additional portion of aminoguanidine bicarbonate (0.60 g, 4.4 mmol) was added. After an additional 22 hours of heating, the reaction was complete. The reaction allowed to cool to ambient temperature, concentrated under reduced pressure and partitioned between ethyl acetate (50 mL) and water (20 mL). The aqueous layer was extracted once more with ethyl acetate (30 mL). The combined organic layers were washed with saturated aqueous NaCl (2×15 mL), dried (Na2SO4), filtered and concentrated. Dichloromethane (5 mL) was added and a precipitate that formed was isolated by filtration, rinsed with dichloromethane (5 mL), and then dried under reduced pressure to afford the title compound as a white powder (1.12 g, 72% yield).

후처리

  1. additionwas added to a 100 mL RBF with a magnetic stirring bar
  2. customThe flask was fitted with a condenser
  3. temperatureThe mixture was heated for 20 hours
  4. temperatureAfter an additional 22 hours of heating
  5. temperatureto cool to ambient temperature
  6. concentrationconcentrated under reduced pressure
  7. custompartitioned between ethyl acetate (50 mL) and water (20 mL)
  8. extractionThe aqueous layer was extracted once more with ethyl acetate (30 mL)
  9. washThe combined organic layers were washed with saturated aqueous NaCl (2×15 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. additionDichloromethane (5 mL) was added
  14. customa precipitate that formed
  15. customwas isolated by filtration
  16. washrinsed with dichloromethane (5 mL)
  17. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-0a2a1c94b35f4b6983e27be13a24dc43
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163027B2

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