Myristyl bromide → HCID 18699148, compound

HRID 266610Notes

Reaction equation

HRID 266610 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:3](=[C:4]23)[CH:2]=1.[OH-].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CS(C)=O>[CH2:42]([N:22]1[C:21](=[O:25])[C:5]2[C:4]3[C:19]4[C:8](=[CH:7][CH:6]=2)[C:9]2[C:20]5[C:13]([CH:12]=[CH:11][CH:10]=2)=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]=4[CH:1]=[CH:2][C:3]=3[C:23]1=[O:24])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29]

Participants

5

Reactant 3

HCID 8208Myristyl bromideHCID 14797Potassium HydroxideHCID 11759047Perylene-3,4-dicarboximide

Product 1

HCID 18699148HCID 18699148, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.40 g (1.25 mmol) of perylene-3,4-dicarboximide and 0.45 g (8 mmol) of KOH powder are suspended in 30 ml of DMSO, 1.38 g of 1-bromotetradecane are added, and the mixture is stirred at room temperature for 90 h. For precipitation, 300 ml of dist. water are added, the precipitated product is filtered off with suction and washed with dist. water and dilute sodium chloride solution. Chromatographic filtration, followed by column chromatography, in each case on silica gel using chloroform, gives a yellow and a red fraction. According to thin-layer chromatography on silica gel using 3:2 xylene/petroleum ether, the yellow fraction contains 3 products having such similar Rf values that no further purification is undertaken. Yield 30 mg. A colour comparison shows that the red fraction is N-(1-tetradecyl)perylene-3,4-dicarboximide. Yield 30 mg (5%) of a red powder showing a strong solid fluorescence. Rf (CHCl3 /silica gel)=0.81.

Workup

  1. customFor precipitation, 300 ml of dist
  2. additionwater are added
  3. filtrationthe precipitated product is filtered off with suction
  4. washwashed with dist
  5. filtrationChromatographic filtration
  6. customgives a yellow and a red fraction
  7. customthat no further purification

Sources & evidence

ORD record
ord-1df3a958b4994fdc9e77b2d1859c2bdb
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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