Water → 2-[4-[Cyano-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]methylene]-2,5-cyclohexadienylidene]malonnitrile

HRID 85325

反応式

HRID 85325 の反応式
[CH:1]1[C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9][C:3](=[C:4]([C:7]#[N:8])[C:5]#N)[CH:2]=1.[CH2:17]([N:21]([CH2:37][CH2:38][CH2:39][CH3:40])[C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]2[S:31]C=[CH:33][CH:34]=2)=[C:24]([O:35][CH3:36])[CH:23]=1)[CH2:18][CH2:19][CH3:20].O.C(OCC)(=O)C>CN(C)C=O>[C:7]([C:4]([C:5]1[S:31][C:30]([CH:29]=[CH:28][C:25]2[CH:26]=[CH:27][C:22]([N:21]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:23][C:24]=2[O:35][CH3:36])=[CH:34][CH:33]=1)=[C:3]1[CH:2]=[CH:1][C:11](=[C:12]([C:15]#[N:16])[C:13]#[N:14])[CH:10]=[CH:9]1)#[N:8]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 73697TetracyanoquinodimethaneHCID 68008836Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

生成物 1

HCID 885492722-[4-[Cyano-[5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]methylene]-2,5-cyclohexadienylidene]malonnitrile収率 14.5%

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 8 ml of N,N-dimethylformamide, 375 mg (1.84 mmol) of 7,7,8,8-tetracyanoquinodimethane 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 hour and further stirred with heating at 50° C. overnight. After the reaction mixture was poured into 80 ml of water, extraction with ethyl acetate, 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 chloroform to give 132 mg of a yellowish white crystal having a mp of 211-214° C. (yield: 14.5%).

後処理

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 1 hour
  3. stirringfurther stirred
  4. washwashing with a saturated saline solution
  5. dry with materialdrying over anhydrous sodium sulfate and concentration
  6. customThe residue was purified by silica gel column chromatography
  7. washwashed with chloroform

出典と根拠

ORDレコード
ord-184ab29b59fb470db7e82cfde172825b
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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