Dimethylformamide → HCID 66823081, compound

HRID 1844287Notes

Reaction equation

HRID 1844287 reaction equation
[CH2:1]([N:5]1[C:12]([C:13]2[S:14][C:15](Br)=[CH:16][CH:17]=2)=[C:11]2[C:7](=[C:8]([C:24]3[S:25][C:26](Br)=[CH:27][CH:28]=3)[N:9]([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]2=[O:19])[C:6]1=[O:30])[CH2:2][CH2:3][CH3:4].[Cu][C:32]#[N:33].[CH3:34][N:35](C=O)C>>[CH2:1]([N:5]1[C:12]([C:13]2[S:14][C:15]([C:34]#[N:35])=[CH:16][CH:17]=2)=[C:11]2[C:7](=[C:8]([C:24]3[S:25][C:26]([C:32]#[N:33])=[CH:27][CH:28]=3)[N:9]([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]2=[O:19])[C:6]1=[O:30])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 66822572HCID 66822572, compound2×HCID 178418546HCID 178418546, compound

Product 1

HCID 66823081HCID 66823081, compound

Procedure

The synthesis of 2,5-di-n-butyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione is described in Zhou et al., Macromolecules 43 (2010) 821-826. 2,5-Di-n-butyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione (1.08 g, 1.89 mmol) and copper(I)-cyanide (4.00 g, 44.6 mmol) in dry DMF (15 mL) are heated under argon at 130° C. for 315 min and at 165° C. for 40 min. The solvent is removed under reduced pressure and the crude product continuously extracted from the reaction mixture with chloroform. The extract is purified by column chromatography (dichloromethane) and washed with hexane affording 333 mg (38%) of a dark violet solid.

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionthe crude product continuously extracted from the reaction mixture with chloroform
  3. customThe extract is purified by column chromatography (dichloromethane)
  4. washwashed with hexane affording 333 mg (38%) of a dark violet solid

Sources & evidence

ORD record
ord-1e67588b0634477f9e4f0e5d1f2a8472
Source dataset
uspto-grants-2015_02
Patent number
US08946376B2

Reaction notes

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