Ethyl orthoformate → 4-ethoxy-3-fluoroanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide

HRID 1593771

반응식

HRID 1593771 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[CH2:17]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=1[F:27])[CH3:18].[CH2:28](OC(OCC)OCC)C>C(O)(C)C>[CH2:17]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][CH:28]=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=2[Cl:16])=[O:5])=[CH:22][C:21]=1[F:27])[CH3:18]

참가 물질

5

반응물 3

HCID 31214Ethyl orthoformate2회HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 195992054-Ethoxy-3-fluoroaniline

생성물 1

HCID 693122634-ethoxy-3-fluoroanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide수율 67%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (5.9 g, 22.7 mmol) in 400 mL of isopropanol was added 4-ethoxy-3-fluoroaniline (3.7 g, 23.8 mmol). This mixture was heated to reflux to give a clear solution. To this solution, triethylorthoformate (11.6 mL, 69.6 mmol) was added dropwise and the reaction mixture was heated at reflux for 18 hours. Additional triethylorthoformate (11.6 mL, 69.6 mmol) was added dropwise and the reaction mixture was heated at reflux for 42 hours. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with ethyl acetate, and dried in vacuo at 40° C. to give 6.4 g (67%) of 4-ethoxy-3-fluoroanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide as a grey solid, mp 245-247° C.; MS 424.1, 426.1 (M+H)+

후처리

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. customto give a clear solution
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 18 hours
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for 42 hours
  8. filtrationthe solid was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried in vacuo at 40° C.

출처 및 근거

ORD 기록
ord-1411a352eaa849ae8ced2bb3a73ce921
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297795B2

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