Water → HCID 67042406, compound

HRID 468708Notes

Reaction equation

HRID 468708 reaction equation
O=[C:2]1[C:6]2=[C:7]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[NH:8][C:9](=[O:10])[C:5]2=[C:4]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[NH:3]1.[C:21]([O-:24])([O-])=O.[K+].[K+].[CH2:27]([CH:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:36]Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].O>CN(C)C=O>[CH2:27]([CH:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:2][N:3]1[C:4]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:5]2[C:6](=[C:7]([C:11]3[S:12][CH:13]=[CH:14][CH:15]=3)[N:8]([CH2:36][CH:35]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:9]2=[O:10])[C:21]1=[O:24])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 231487459-(BroMoMethyl)nonadecaneHCID 1785175291,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione

Product 1

HCID 67042406HCID 67042406, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a three-neck, oven dried, 250 ml round bottom flask, 2,5-dihydro-1,4-dioxo-3,6-dithienylpyrrolo[3,4-c]-pyrrole (2), (7.0 g. 23.30 mmol) and anhydrous K2CO3 (8.95 g, 69.91 mmol) were dissolved in 250 ml of anhydrous N,N-dimethylformamide (DMF), and heated to 120° C. under argon for 1 h. 2-octyl-1-dodecylbromide (25.27 g, 69.91 mmol) was then added dropwise, and the reaction mixture was further stirred and heated overnight at 130° C. The reaction mixture was cooled to room temperature and then poured into water and stirred for 30 minutes. The product was extracted with chloroform, then successively washed with water, and dried over MgSO4. Removal of the solvent afforded the crude product which was then purified using column chromatography on silica gel using a mixture of hexane and chloroform as eluent, giving a purple solid (11.0 g, 54%). 1H NMR (CDCl3): (0.87 (t, 12H), 1.13-1.45 (m, 64H), 1.89 (s, 2H), 4.00 (d, 4H), 7.26 (d, 2H), 7.52 (d, 2H), 8.87 (d, 2H). MS (MALDI-TOF) m/z 860.63 (M). calcd. for C54H88N2O2S2=860.25.

Workup

  1. customIn a three-neck, oven dried
  2. temperatureheated overnight at 130° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringstirred for 30 minutes
  5. extractionThe product was extracted with chloroform
  6. washsuccessively washed with water
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent
  9. customafforded the crude product which
  10. customwas then purified
  11. additiona mixture of hexane and chloroform as eluent

Sources & evidence

ORD record
ord-05907aa3aad04f1d92365932685da392
Source dataset
uspto-grants-2014_01
Patent number
US08624232B2

Reaction notes

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