Hydrochloric Acid → Ethyl[(Z)-2-cyano-1-(2,4-difluorophenyl)ethenyl]carbamate

HRID 2088671노트

반응식

HRID 2088671 반응식
[Na].[NH2:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[F:14])=[CH:4][C:5]#[N:6].[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:17]([O:16][C:15](=[O:19])[NH:2]/[C:3](/[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[F:14])=[CH:4]\[C:5]#[N:6])[CH3:18]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 667253443-Amino-3-(2,4-difluorophenyl)prop-2-enenitrile

생성물 1

HCID 58305996Ethyl[(Z)-2-cyano-1-(2,4-difluorophenyl)ethenyl]carbamate

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

At 40° C., 769 mg (33.44 mmol) of sodium were dissolved in ethanol (41 ml). 4.14 g (22.29 mmol) of 3-amino-3-(2,4-difluorophenyl)prop-2-enonitrile and 5.79 g (49 mmol) of diethyl carbonate were added, and the reaction solution was stirred under reflux for 4 h. 200 ml of ethyl acetate and 150 ml of water were added to the reaction mixture and the pH was adjusted with hydrochloric acid to pH=5. The organic phase was separated off, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was triturated with diisopropyl ether and the white precipitate was filtered off with suction. More product was obtained by separating the mother liquor by preparative HPLC (Method 11). Drying under high vacuum gave a total of 4.92 g (49% of theory) of the product as a mixture of E and Z isomers which was used without further purification.

후처리

  1. temperatureunder reflux for 4 h
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationthe white precipitate was filtered off with suction
  7. customMore product was obtained
  8. customby separating the mother liquor by preparative HPLC (Method 11)
  9. customDrying under high vacuum
  10. customgave a total of 4.92 g (49% of theory) of the product
  11. additionas a mixture of E and Z isomers which
  12. customwas used without further purification

출처 및 근거

ORD 기록
ord-2f4f357b73274f0f9807f875eeafd29f
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436003B2

반응 노트

불러오는 중…