Cesium carbonate → HCID 70496115, compound

HRID 1909829Notes

Reaction equation

HRID 1909829 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].Br[CH2:46][CH:47]([CH2:50][CH2:51][CH2:52][CH3:53])[CH2:48][CH3:49].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:32]([C:30]1[CH:31]=[C:27]([C:22]2[N:23]([CH2:17][CH:13]([CH2:14][CH3:15])[CH2:1][CH2:2][CH2:3][CH3:4])[C:24](=[O:26])[C:25]3[C:21]=2[C:20](=[O:44])[N:19]([CH2:46][CH:47]([CH2:48][CH3:49])[CH2:50][CH2:51][CH2:52][CH3:53])[C:18]=3[C:15]2[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]=2)[S:28][CH:29]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 868042-Ethylhexyl bromideHCID 178442827HCID 178442827, compound

Product 1

HCID 70496115HCID 70496115, compoundYield 21.3%

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 (1.91 g, 3.0 mmol), 3-bromomethyl-heptane (1.54 g, 8.0 mmol), Cs2CO3 (2.93 g, 9.0 mmol) and then purged with argon for 10 minutes before 100 mL of dimethylformamide (DMF) was added. The mixture was heated at 60° C. overnight and then cooled to room temperature. Dichloromethane (50 mL) was added. The organic layer was washed with water (50 mL for 3 times) and 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) as the eluent and weighed 0.55 g (overall yield: 21.3% from 4-dodecyl-thiophene-2-carbonitrile 3) after being dried.

Workup

  1. custompurged with argon for 10 minutes before 100 mL of dimethylformamide (DMF)
  2. additionwas added
  3. temperaturecooled to room temperature
  4. additionDichloromethane (50 mL) was added
  5. washThe organic layer was washed with water (50 mL for 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) as the eluent
  10. customafter being dried

Sources & evidence

ORD record
ord-69a07db314a341b9ac32ec83c0118224
Source dataset
uspto-grants-2013_12
Patent number
US08598450B2

Reaction notes

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