Water → HCID 18329404, compound

HRID 1250011Notes

Reaction equation

HRID 1250011 reaction equation
[CH3:1]N(C)C=O.O([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[CH:17][CH:16]=[C:15]2[C:24]2[S:25][C:26]([CH:29]=[C:30]([C:33]#[N:34])[C:31]#[N:32])=[CH:27][CH:28]=2)=[CH:10][CH:9]=1)C.[C:35]([C:37]([C:43]#[N:44])=[C:38](C#N)[C:39]#[N:40])#[N:36].[OH2:45]>>[CH3:1][O:45][C:12]1[CH:13]=[CH:8][CH:9]=[CH:10][C:11]=1[N:14]1[C:18]([C:19]2[S:20][C:21]([C:38]([C:39]#[N:40])=[C:37]([C:43]#[N:44])[C:35]#[N:36])=[CH:22][CH:23]=2)=[CH:17][CH:16]=[C:15]1[C:24]1[S:25][C:26]([CH:29]=[C:30]([C:33]#[N:34])[C:31]#[N:32])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 12635TetracyanoethyleneHCID 18329401HCID 18329401, compound

Product 1

HCID 18329404HCID 18329404, compound

Procedure

Into N, N-dimethylformamide (10 ml) was dissolved 1-(4-methoxylphenyl)-2-[5-(2,2-dicyanoethenyl)-2-thienyl]-5-(2-thienyl)pyrrole (53.7 mg). After tetracyanoethylene (35.3 mg: 2.1 mol equivalents) was added to the solution, it was stirred at room temperature for 21 hours and further at 80° for 18 hours. Into the reaction mixture was added 50 ml of water, which was then extracted with chloroform (50 ml×3). The combined organic layers were subjected to drying over anhydrous magnesium sulfate and condensation under reduced pressure. The resulting residue was separated by column chromatography (silica gel, chloroform), and 1-(methoxyphenyl)-2-[5-(2,2-dicyanoethenyl)-2-thienyl]-5-[5-(tricyanoethenyl)-2-thienyl]pyrrole was obtained (31.8 mg, 0.0618 mmol., 48%). The product had the following physical values.

Workup

  1. extractionwas then extracted with chloroform (50 ml×3)
  2. dry with materialto drying over anhydrous magnesium sulfate and condensation under reduced pressure
  3. customThe resulting residue was separated by column chromatography (silica gel, chloroform)

Sources & evidence

ORD record
ord-bf7d35e8774349af8f9d63227a5d87c0
Source dataset
uspto-grants-2002_01
Patent number
US06335452B2

Reaction notes

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