Methacryloyl chloride → HCID 22725845, compound

HRID 348227Notes

Reaction equation

[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:33](=[O:34])[C:30]2[C:31]3[C:32]4[C:27](=[CH:28][CH:29]=2)[C:26]2[C:35]5[C:22]([CH:23]=[CH:24][CH:25]=2)=[CH:21][CH:20]=[CH:19][C:18]=5[C:17]=4[CH:16]=[CH:15][C:14]=3[C:12]1=[O:13])(=[O:4])[CH:2]=[CH2:3].[C:36](Cl)(=O)C(C)=C>N1C=CC=CC=1.O1CCOCC1>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:33](=[O:34])[C:30]2[C:31]3[C:32]4[C:27](=[CH:28][CH:29]=2)[C:26]2[C:35]5[C:22]([CH:23]=[CH:24][CH:25]=2)=[CH:21][CH:20]=[CH:19][C:18]=5[C:17]=4[CH:16]=[CH:15][C:14]=3[C:12]1=[O:13])(=[O:4])[C:2]([CH3:36])=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

2 g (5 mmol) of N-(5-hydroxypentyl)perylene-3,4-dicarboximide from Example 7, 1. were dissolved in 60 ml of pyridine under nitrogen, with heating at 80° C., and the solution was admixed dropwise at this temperature with a solution of 0.97 ml (10 mmol) of methacryloyl chloride in 30 ml of anhydrous dioxane. Stirring was continued at 80° C. for a further 1.5 h, the solvent was removed by distillation, the residue was taken up in 30 ml of chloroform, a filtration was conducted, the filtrate was admixed with 100 ml of hexane and the precipitated product was isolated by filtration. Chromatographic purification on a short silica gel column using methylene chloride as eluent gave 1.6 g (70%) of the desired product as a brownish red powder.

Workup

customthe solvent was removed by distillation
filtrationa filtration
customthe precipitated product was isolated by filtration
customChromatographic purification on a short silica gel column

Sources & evidence

ORD record: ord-a8f0803a29ab432dab78849a985b5416
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176255B2

Reaction notes

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