Dimethylformamide → HCID 86756220, compound

HRID 565729Notes

Reaction equation

HRID 565729 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:17][CH:16]=[C:15]1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:5][CH3:6].CN(C)C=O.[C:34]([C:36]([C:42]#[N:43])=[C:37](C#N)[C:38]#[N:39])#[N:35]>O>[CH3:1][CH2:2][CH2:3][CH:4]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18]([C:19]2[S:20][C:21]([C:37]([C:38]#[N:39])=[C:36]([C:42]#[N:43])[C:34]#[N:35])=[CH:22][CH:23]=2)=[CH:17][CH:16]=[C:15]1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12635TetracyanoethyleneHCID 70100439HCID 70100439, compound

Product 1

HCID 86756220HCID 86756220, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After dissolving 1-[(4-n-hexyloxy)phenyl]-2,5-bis(2-thienyl)pyrrole (205 mg) into N,N-dimetylformamide (30 ml), tetracyanoethylene (126 mg) was added thereto, and then they were stirred for 24 hours at room temperature. After addition of water thereinto, extraction by toluene was conducted. The obtained organic layer is dried over anhydrous sodium sulfate, and then condensation thereof under vacuum was conducted. Subsequently, the condensed substance is separated by silica gel column chromatography using toluene as eluent to obtain 1-[(4-n-hexyloxy)phenyl]-2-(2-thienyl)-5-(5-tricyanoethenyl-2-thienyl)pyrrole (212 mg, yield 83%). After recrystallization from a chloroform-hexane mixture solvent, crystals having a bronzy metallic luster were obtained. FIG. 1 is a photograph showing the appearance of the crystals. Further, physical properties thereabout are shown bellow.

Workup

  1. additionwas added
  2. extractionextraction by toluene
  3. dry with materialThe obtained organic layer is dried over anhydrous sodium sulfate
  4. customcondensation
  5. customSubsequently, the condensed substance is separated by silica gel column chromatography

Sources & evidence

ORD record
ord-2abe2423e7ad44f3a91165e5c3354e2b
Source dataset
uspto-grants-2001_01
Patent number
US06172240B2

Reaction notes

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