Cesium carbonate → HCID 86668273, compound

HRID 1909830Notes

Reaction equation

HRID 1909830 reaction equation
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]2[NH:19][C:20](=[O:44])[C:21]3[C:25]=2[C:24](=[O:26])[NH:23][C:22]=3[C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:31]=2)[S:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].I[CH2:46][CH:47]([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:48][CH2:49][CH2:50][CH3:51].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:48]([CH:47]([CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:46][N:23]1[C:22]([C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH:31]=2)=[C:21]2[C:25](=[C:18]([C:15]3[S:16][CH:17]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=3)[N:19]([CH2:17][CH:13]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:14][CH2:15][CH2:18][CH2:25][CH2:21][CH3:20])[C:20]2=[O:44])[C:24]1=[O:26])[CH2:49][CH2:50][CH3:51]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 58434872HCID 58434872, compoundHCID 178442827HCID 178442827, compound

Product 1

HCID 86668273HCID 86668273, compoundYield 21.7%

Conditions

Temperature
60 °C

Procedure

A 100 mL flask was charged with 3,6-bis-(4-dodecyl-thiophen-2-yl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 4 (4.3 g, 6.75 mmol), 5-iodomethyl-undecane (6.22 g, 21.0 mmol), Cs2CO3 (7.82 g, 24.0 mmol) and then purged with argon for 10 minutes before 150 mL of dimethylformamide (DMF) was added. The mixture was heated at 60° C. for 36 hours, then at 90° C. for 8 hours, and cooled to room temperature before 200 mL of hexane was added. The organic layer was washed with water (200 mL, 3 times), then dried over anhydrous Na2SO4. Black solids were obtained after removal of the solvent and precipitation from methanol. The product was purified by column with dichloromethane/hexane (v/v: 2/1 with Rf=0.25) as the eluent and weighed 1.43 g (21.7% yield from 4-dodecyl-thiophene-2-carbonitrile 3) after drying.

Workup

  1. custompurged with argon for 10 minutes before 150 mL of dimethylformamide (DMF)
  2. additionwas added
  3. temperaturecooled to room temperature before 200 mL of hexane
  4. additionwas added
  5. washThe organic layer was washed with water (200 mL, 3 times)
  6. dry with materialdried over anhydrous Na2SO4
  7. customBlack solids were obtained
  8. customafter removal of the solvent and precipitation from methanol
  9. customThe product was purified by column with dichloromethane/hexane (v/v: 2/1 with Rf=0.25) as the eluent
  10. customafter drying

Sources & evidence

ORD record
ord-65c7a45833a84c02bb46578beef9864d
Source dataset
uspto-grants-2013_12
Patent number
US08598450B2

Reaction notes

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