Acryloyl chloride → HCID 22725846, compound
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:29](=[O:30])[C:26]2[C:27]3[C:28]4[C:23](=[CH:24][CH:25]=2)[C:22]2[C:31]5[C:18]([CH:19]=[CH:20][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=5[C:13]=4[CH:12]=[CH:11][C:10]=3[C:8]1=[O:9].[C:32](Cl)(=[O:35])[CH:33]=[CH2:34]>N1C=CC=CC=1.O1CCOCC1.C(Cl)Cl>[C:32]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:9])[C:10]2[C:27]3[C:28]4[C:13](=[CH:12][CH:11]=2)[C:14]2[C:31]5[C:18]([CH:17]=[CH:16][CH:15]=2)=[CH:19][CH:20]=[CH:21][C:22]=5[C:23]=4[CH:24]=[CH:25][C:26]=3[C:29]1=[O:30])(=[O:35])[CH:33]=[CH2:34]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
2 g (5 mmol) of N-(5-hydroxypentyl)perylene-3,4-dicarboximide from 1. were dissolved under nitrogen in 60 ml of pyridine, with heating at 80° C., cooled to 65° C. and admixed dropwise at this temperature with a solution of 0.81 ml (10 mmol) of acryloyl chloride in 30 ml of anhydrous dioxane. The mixture was stirred at 65° C. for a further 1.5 h, the solvent was removed by distillation, the residue was taken up in 20 ml of chloroform, a filtration was conducted, the filtrate was admixed with 100 ml of hexane, and the precipitated product was isolated by filtration. Chromatography on a short silica gel column using methylene chloride as eluent gave 1.5 g (65%) of the desired product as a brownish red powder with a strong tendency to polymerize on heating.
Workup
- temperaturecooled to 65° C.
- customthe solvent was removed by distillation
- filtrationa filtration
- customthe precipitated product was isolated by filtration
Sources & evidence
- ORD record
- ord-2b2b0944728648f08510d01cc48bd46c
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727318B1
Reaction notes
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