Tetracyanoquinodimethane → 2-[4-[Cyano-(4-dibutylamino-2-methoxyphenyl)methylene]-2,5-cyclohexadienylidene]malonnitrile

HRID 85324

반응식

HRID 85324 반응식
[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]([CH2:30][CH2:31][CH2:32][CH3:33])[C:22]1[CH:27]=[CH:26]C=[C:24]([O:28][CH3:29])[CH:23]=1)[CH2:18][CH2:19][CH3:20]>CN(C)C=O>[C:7]([C:4]([C:5]1[CH:26]=[CH:27][C:22]([N:21]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][C:24]=1[O:28][CH3:29])=[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]

참가 물질

4

반응물 2

HCID 73697TetracyanoquinodimethaneHCID 4068285N,N-Dibutyl-3-methoxybenzenamine

생성물 1

HCID 885493652-[4-[Cyano-(4-dibutylamino-2-methoxyphenyl)methylene]-2,5-cyclohexadienylidene]malonnitrile수율 25.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

In 8 ml of N,N-dimethylformamide, 460 mg (2.25 mmol) of 7,7,8,8-tetracyanoquinodimethane was dissolved. With stirring under ice cooling, 500 mg (2.12 mmol) of dibutyl(3-methoxyphenyl)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 further stirred for 3.5 hours. After the reaction mixture was poured into 100 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 226 mg of an off-white crystal having a mp of 215-238° C. (yield: 25.6%).

후처리

  1. additionadded dropwise
  2. stirringThe mixture was stirred for 1.5 hours
  3. customAfter the ice bath was removed
  4. stirringthe mixture was further stirred for 3.5 hours
  5. additionAfter the reaction mixture was poured into 100 ml of water, extraction with ethyl acetate
  6. washwashing with a saturated saline solution
  7. dry with materialdrying over anhydrous sodium sulfate, and concentration
  8. customThe residue was purified by silica gel column chromatography
  9. washwashed with chloroform

출처 및 근거

ORD 기록
ord-8d622d8f878347c09f01224d029dd60f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846955B2

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