Dimethylformamide → HCID 66822907, compound

HRID 1844289Notes

Reaction equation

HRID 1844289 reaction equation
[CH2:1]([N:7]1[C:14]([C:15]2[S:16][C:17](Br)=[CH:18][CH:19]=2)=[C:13]2[C:9](=[C:10]([C:28]3[S:29][C:30](Br)=[CH:31][CH:32]=3)[N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2=[O:21])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cu][C:36]#[N:37].[CH3:38][N:39](C=O)C>>[CH2:1]([N:7]1[C:14]([C:15]2[S:16][C:17]([C:38]#[N:39])=[CH:18][CH:19]=2)=[C:13]2[C:9](=[C:10]([C:28]3[S:29][C:30]([C:36]#[N:37])=[CH:31][CH:32]=3)[N:11]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2=[O:21])[C:8]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 668228943,6-Bis(5-bromothiophen-2-yl)-2,5-dihexyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione2×HCID 178418546HCID 178418546, compound

Product 1

HCID 66822907HCID 66822907, compound

Conditions

Temperature
130 °C

Procedure

The synthesis of 2,5-di-n-hexyl-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-hexyl-3,6-bis(5-bromo-thiophen-2-yl)pyrrolo[3,4-c]-pyrrole-1,4-dione (237 mg, 0.378 mmol) and copper(I)-cyanide (1.50 g, 17.0 mmol) are placed in a 25 mL-flask under argon. Dry DMF (10 mL) is added and the mixture is stirred at 130° C. for 4 h. The solvent is removed under reduced pressure and the residual solid is extracted with chloroform (250 mL). After removing the solvent the crude product is purified by column chromatography (dichloromethane). A violet solid is obtained (52 mg, 27%).

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionthe residual solid is extracted with chloroform (250 mL)
  3. customAfter removing the solvent the crude product
  4. customis purified by column chromatography (dichloromethane)
  5. customA violet solid is obtained (52 mg, 27%)

Sources & evidence

ORD record
ord-12533007a2494a5b9739efc60514a263
Source dataset
uspto-grants-2015_02
Patent number
US08946376B2

Reaction notes

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