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

HRID 1593771ノート

反応式

HRID 1593771 の反応式
[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]

参加物

5

反応物 3

HCID 31214Ethyl orthoformate2 回HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 195992054-Ethoxy-3-fluoroaniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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)+

後処理

  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.

出典と根拠

ORDレコード
ord-1411a352eaa849ae8ced2bb3a73ce921
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

反応ノート

読み込み中…