Dimethylformamide → HCID 66822730, compound

HRID 1844288Notes

Reaction equation

HRID 1844288 reaction equation
[CH2:1]([N:6]1[C:13]([C:14]2[S:15][C:16](Br)=[CH:17][CH:18]=2)=[C:12]2[C:8](=[C:9]([C:26]3[S:27][C:28](Br)=[CH:29][CH:30]=3)[N:10]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]2=[O:20])[C:7]1=[O:32])[CH2:2][CH2:3][CH2:4][CH3:5].[Cu][C:34]#[N:35].[CH3:36][N:37](C=O)C>>[CH2:1]([N:6]1[C:13]([C:14]2[S:15][C:16]([C:36]#[N:37])=[CH:17][CH:18]=2)=[C:12]2[C:8](=[C:9]([C:26]3[S:27][C:28]([C:34]#[N:35])=[CH:29][CH:30]=3)[N:10]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]2=[O:20])[C:7]1=[O:32])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 66822534HCID 66822534, compound2×HCID 178418546HCID 178418546, compound

Product 1

HCID 66822730HCID 66822730, compound

Procedure

The synthesis of 2,5-di-n-pentyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione is done in analogy to Zhou et al., Macromolecules 43 (2010) 821-826. 2,5-Di-n-pentyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione (600 mg, 1.00 mmol) and copper(I)-cyanide (1.60 g, 18.0 mmol) in dry DMF (15 mL) are heated under argon at 120° C. for 60 min and at 165° C. for 80 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 64.0 mg (13%) 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 64.0 mg (13%) of a dark violet solid

Sources & evidence

ORD record
ord-3f26b686264942de8770c33b5222815e
Source dataset
uspto-grants-2015_02
Patent number
US08946376B2

Reaction notes

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