Toluene → N-(2-octyldodecyl)-2,2'-bithiophene-3,3'-dicarboximide

HRID 536991Notes

Reaction equation

HRID 536991 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([O:8][C:9]([C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:2]1=2)=[O:10])=O.C1(C)C=CC=CC=1.[CH2:23]([CH:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:32][NH2:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CN(C)C1C=CN=CC=1.C(OCC)C>[CH2:23]([CH:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:32][N:33]1[C:6](=[O:8])[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:9]1=[O:10])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 1140TolueneHCID 187619992-n-Octyl-1-dodecylamineHCID 89807128Dithieno(3,2-c:2',3'-e)oxepine-4,6-dione

Product 1

HCID 117636372N-(2-octyldodecyl)-2,2'-bithiophene-3,3'-dicarboximideYield 187.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A dry 8 mL microwave reaction tube was charged with a micro-stirbar, anhydride (4) (354 mg, 1.50 mmol), 4-(dimethylamino)pyridine (61 mg, 0.50 mmol), and 5 mL of toluene. Next, 2-octyldodecylamine (446 mg, 1.5 mmol) was added dropwise to the suspension over 15 minutes and the reaction was allowed to stir for an additional 15 minutes until no solid remained. The reaction tube was then irradiated with microwaves (PMAX=300 W) for 2 hours at a constant temperature of 220° C. This procedure was repeated four more times and the five reaction mixtures were combined in 250 mL of diethyl ether, washed six times with 150 mL of water, one time with 100 mL of brine, and the organics dried over Mg2SO4. After filtration, the solvent was removed by evaporation to afford a yellow oil (90% pure by 1H NMR) that was purified by column chromatography on silica gel with a mixture of diethyl ether (10%) and hexane (90%) as the eluent. A light yellow oil (1.45 g, 37% yield) was obtained upon concentration of the main fractions.

Workup

  1. customA dry 8 mL microwave reaction tube
  2. customThe reaction tube was then irradiated with microwaves (PMAX=300 W) for 2 hours at a constant temperature of 220° C
  3. customthe five reaction mixtures
  4. washwashed six times with 150 mL of water, one time with 100 mL of brine
  5. dry with materialthe organics dried over Mg2SO4
  6. filtrationAfter filtration
  7. customthe solvent was removed by evaporation
  8. customto afford a yellow oil (90% pure by 1H NMR) that
  9. customwas purified by column chromatography on silica gel with a mixture of diethyl ether (10%) and hexane (90%) as the eluent

Sources & evidence

ORD record
ord-8091c8503e4b44ed8b99f09c1688f07e
Source dataset
uspto-grants-2014_10
Patent number
US08859714B1

Reaction notes

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