Water → HCID 22725853, compound

HRID 348229Notes

Reaction equation

HRID 348229 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]1[C:35](=[O:36])[C:32]2[C:33]3[C:34]4[C:29](=[CH:30][CH:31]=2)[C:28]2[C:37]5[C:24]([C:25]([C:38]#[C:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[CH:18]=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:52](Cl)(=[O:56])[C:53]([CH3:55])=[CH2:54].O>O1CCOCC1>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[N:13]1[C:35](=[O:36])[C:32]2[C:33]3[C:34]4[C:29](=[CH:30][CH:31]=2)[C:28]2[C:37]5[C:24]([C:25]([C:38]#[C:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][C:52](=[O:56])[C:53]([CH3:55])=[CH2:54])=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[CH:18]=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chloride2×HCID 22725866HCID 22725866, compound

Product 1

HCID 22725853HCID 22725853, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 1 g (1.72 mmol) of N-(2,6-diisopropylphenyl)-9-(6-hydroxy-1-hexynyl)perylene-3,4-dicarboximide in 100 ml of dry dioxane was heated to 45° C. under nitrogen, admixed with 0.4 ml of triethylamine and 0.28 ml of methacryloyl chloride, stirred at 45° C. for 4 h, admixed with 0.28 ml of methacryloyl chloride, stirred at 45° C. for a further 12 h, cooled to room temperature, again admixed with 200 ml of water and extracted with a total of 400 ml of methylene chloride. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel using methylene chloride as eluent. Following removal of the solvent under reduced pressure, 800 mg (78%) of the desired product were isolated as a red, finely crystalline solid.

Workup

  1. stirringstirred at 45° C. for a further 12 h
  2. temperaturecooled to room temperature
  3. extractionextracted with a total of 400 ml of methylene chloride
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5861be9a433f4ad888d42f5baa1849b1
Source dataset
uspto-grants-2007_02
Patent number
US07176255B2

Reaction notes

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