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Ethyl orthoformate → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide

HRID 1593774
ノート
印刷プレビュー

反応式

HRID 1593774 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].[I:17][C:18]1[CH:19]=[C:20]([NH2:29])[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH2:26][O:27][CH3:28].[CH2:30](OC(OCC)OCC)C>C(O)(C)C>[C:1]([C:3](=[CH:30][NH:29][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][O:27][CH3:28])=[C:18]([I:17])[CH:19]=1)[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 31214Ethyl orthoformate2 回HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamideHCID 660942063-Iodo-4-(2-methoxyethoxy)aniline

生成物 1

HCID 693123182-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide収率 78.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (3.2 g, 12.4 mmol) and [3-iodo-4-(2-methoxyethoxy)phenyl]amine (4.0 g, 13.7 mmol) in 350 mL of iso-propanol was heated to reflux and triethylorthoformate (5.6 mL, 33.7 mmol) was added dropwise. The reaction mixture was heated at reflux for 3 hours. Additional triethylorthoformate (2.0 mL, 12.0 mmol) was added dropwise and the reaction mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with iso-propanol, diethyl ether, and ethyl acetate and then dried in vacuo to give 5.5 g of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-{[3-iodo-4-(2-methoxyethoxy)phenyl]amino}acrylamide as a yellow solid, mp 209-210° C.; MS (ES) 560.0, 562.1 (M−H)−

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 3 hours
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux overnight
  7. filtrationthe solid was collected by filtration
  8. washwashed with iso-propanol, diethyl ether, and ethyl acetate
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-91a3f71283404d0bac78272c45df537c
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07297795B2

反応ノート

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