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

HRID 1593768ノート

反応式

HRID 1593768 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].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[NH2:21].[CH2:27](OC(OCC)OCC)C>C(O)(C)C>[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[NH:21][CH:27]=[C:3]([C:1]#[N:2])[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]

参加物

5

反応物 3

HCID 31214Ethyl orthoformateHCID 9610833-Bromo-4-methoxyanilineHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

生成物 1

HCID 693135643-bromo-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide収率 23.1%

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 (900 mg, 3.46 mmol) in 100 mL of iso-propanol was added 3-bromo-4-methoxyaniline (700 mg, 3.46 mmol). This mixture was heated to reflux and triethylorthoformate (3.3 mL, 19.8 mmol) was added dropwise. The reaction mixture was heated at reflux for 6 hours. The mixture was filtered while still warm and the collected white solid was washed with iso-propanol to give 376 mg of 3-bromo-4-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide, mp >250° C.; MS (ES) m/z 467.7, 469.9, 471.7 (M−H)−

後処理

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 6 hours
  5. filtrationThe mixture was filtered
  6. temperaturewhile still warm
  7. washthe collected white solid was washed with iso-propanol

出典と根拠

ORDレコード
ord-59b11ceb94e84cbda3077a4ab51c9502
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

反応ノート

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