Hydrochloric Acid → HCID 22725850, compound

HRID 348224Notes

Reaction equation

HRID 348224 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](=[C:30](Br)[CH:31]=2)[C:28]2[C:38]5[C:24]([C:25](Br)=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[C:18](Br)=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:3])[CH3:2].[C:41]([C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1)([CH3:44])([CH3:43])[CH3:42].[C:52](=[O:55])([O-])[O-].[K+].[K+].Cl>CN1CCCC1=O>[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](=[C:30]([O:51][C:48]5[CH:47]=[CH:46][C:45]([C:41]([CH3:44])([CH3:42])[CH3:43])=[CH:50][CH:49]=5)[CH:31]=2)[C:28]2[C:38]5[C:24]([C:25]([O:51][C:48]6[CH:47]=[CH:46][C:45]([C:41]([CH3:44])([CH3:42])[CH3:43])=[CH:50][CH:49]=6)=[CH:26][CH:27]=2)=[CH:23][CH:22]=[CH:21][C:20]=5[C:19]=4[C:18]([O:55][C:52]2[CH:49]=[CH:50][C:45]([C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:46][CH:47]=2)=[CH:17][C:16]=3[C:14]1=[O:15])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 87695054HCID 87695054, compound

Product 1

HCID 22725850HCID 22725850, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 32.3 g (45 mmol) of N-(2,6-diisopropylphenyl)-1,6,9-tribromoperylene-3,4-dicarboximide (prepared in accordance with Example 1a of WO 96/22 332), 27.0 g (180 mmol) of p-tert-butylphenol, 16.6 g (120 mmol) of anhydrous, finely pulverized potassium carbonate and 1200 ml of N-methylpyrrolidone (NMP) was heated at 120° C. with stirring for 6 h. After cooling to room temperature, the reaction mixture was introduced with stirring into 4500 g of 6% strength by weight aqueous hydrochloric acid, the mixture was subsequently stirred for 2 h, and the precipitated solid was filtered off, washed to neutrality with water and dried under reduced pressure at 100° C. Filtration through a short silica gel column using methylene chloride as eluent, and removal of the solvent under reduced pressure, gave 38.9 g (93%) of the desired product in the form of reddish violet crystals having a softening point of 156° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was introduced
  3. stirringthe mixture was subsequently stirred for 2 h
  4. filtrationthe precipitated solid was filtered off
  5. washwashed
  6. customdried under reduced pressure at 100° C
  7. filtrationFiltration through a short silica gel column
  8. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-45296fbcd7d1488792f8e293a89e5e23
Source dataset
uspto-grants-2007_02
Patent number
US07176255B2

Reaction notes

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