Tetracyanoethylene → 2-Cyano-3-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]-2-butenedinitrile

HRID 85323

反応式

HRID 85323 の反応式
[C:1]([C:3]([C:9]#[N:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])#N.[CH2:11]([N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]2[S:25]C=[CH:27][CH:28]=2)=[C:18]([O:29][CH3:30])[CH:17]=1)[CH2:12][CH2:13][CH3:14]>CN(C)C=O>[C:5]([C:4](=[C:3]([C:1]1[S:25][C:24]([CH:23]=[CH:22][C:19]2[CH:20]=[CH:21][C:16]([N:15]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][C:18]=2[O:29][CH3:30])=[CH:28][CH:27]=1)[C:9]#[N:10])[C:7]#[N:8])#[N:6]

参加物

4

反応物 2

HCID 12635TetracyanoethyleneHCID 68008836Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

生成物 1

HCID 866676052-Cyano-3-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]-2-butenedinitrile収率 41.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

In 7 ml of N,N-dimethylformamide, 235 mg (1.83 mmol) of tetracyanoethylene was dissolved. With stirring under ice cooling, 600 mg (1.75 mmol) of dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine was dissolved in 2 ml of N,N-dimethylformamide and added dropwise. The mixture was stirred for 1.5 hours. After the ice bath was removed, the mixture was stirred at room temperature for 1 hour and further stirred with heating at 50° C. overnight. After the reaction mixture was poured into 80 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography and washed with methanol to give 324 mg of a dark reddish crystal having a mp of 189-192° C. (yield: 41.8%).

後処理

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 1.5 hours
  3. customAfter the ice bath was removed
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringfurther stirred
  6. additionAfter the reaction mixture was poured into 80 ml of water, extraction with chloroform
  7. washwashing with a saturated saline solution
  8. dry with materialdrying over anhydrous sodium sulfate, and concentration
  9. customThe residue was purified by silica gel column chromatography
  10. washwashed with methanol
  11. customto give 324 mg of a dark reddish crystal

出典と根拠

ORDレコード
ord-a674ceb4ec954a34a54c2ac91ef6271e
出典データセット
uspto-grants-2014_09
特許番号
US08846955B2

関連ノート

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