Triethylamine → HCID 178427727, compound

HRID 1410516Notes

Reaction equation

HRID 1410516 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]([C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:38]=3[C:28]([C:29]3[C:34]=2[C:33]=1[C:32]([C:35]([OH:37])=[O:36])=[CH:31][CH:30]=3)=[CH:27][CH:26]=[C:25]4Br)[OH:15])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:47]([O:53][S:54]([C:57]1[CH:62]=[CH:61][C:60]([CH3:63])=[CH:59][CH:58]=1)(=[O:56])=[O:55])[CH2:48][CH2:49][CH2:50][C:51]#[CH:52]>CN(C)C=O.C(Cl)Cl.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]=[C:14]([C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[C:24]4[C:38]=3[C:28]([C:29]3[C:34]=2[C:33]=1[C:32]([C:35]([OH:37])=[O:36])=[CH:31][CH:30]=3)=[CH:27][CH:26]=[C:25]4[C:52]#[C:51][CH2:50][CH2:49][CH2:48][CH2:47][O:53][S:54]([C:57]1[CH:58]=[CH:59][C:60]([CH3:63])=[CH:61][CH:62]=1)(=[O:55])=[O:56])[OH:15])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11097066HCID 11097066, compoundHCID 178439045HCID 178439045, compound

Product 1

HCID 178427727HCID 178427727, compound

Reagents, catalysts & solvents 3

HCID 178420553HCID 178420553, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a degassed mixture of 2.40 g (4.32 mmoles) of N-(2,6-diisopropylphenyl)-9-bromo-perylene-3,4-dicarboxylic acid imide (synthesized according to WO2001016109) and 0.576 g (3.36 mmoles) of Cu(I) iodide in 72 ml dimethylformamide (DMF) and 144 ml methylene chloride were added 2.00 g (1.72 mmoles) of tetrakis(triphenylphosphino)-palladium (0), 2.09 g (2.88 ml, 2.05 mmol) triethylamine and a degassed solution of 1.82 g (7.20 mmol) p-toluensulfonic acid-5-hexinyl ester (synthesized according to (Y. Yang and T. M. Swager, Macromolecules 2006, 39, 2013-2015) in 12 ml methylene chloride. The reaction mixture was stirred for 90 minutes at room temperature, subsequently the solvent was evaporated until dryness and purified on silica gel (solvent: toluene:methylene chloride:10:1 to 1:1). 2.04 g (65% of the theoretical yield) of a red solid were obtained.

Workup

  1. customsubsequently the solvent was evaporated until dryness
  2. custompurified on silica gel (solvent: toluene:methylene chloride:10:1 to 1:1)
  3. custom2.04 g (65% of the theoretical yield) of a red solid
  4. customwere obtained

Sources & evidence

ORD record
ord-5f2acbbafcf14237823630649442e082
Source dataset
uspto-grants-2014_12
Patent number
US08921558B2

Reaction notes

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