Dimethyl Sulfate → Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

HRID 2051383

Reaktionsgleichung

Reaktionsgleichung von HRID 2051383
[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH:18][C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:24]OS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([N:18]([CH3:24])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 7730236N-(4-Bromo-9,10-dioxo-9,10-dihydroanthracen-1-YL)acetamide

Produkt 1

HCID 80770Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-Ausbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), monochlorobenzene (420 g), tetra-n-butyl ammonium bromide (0.3 g) and 98.5% sodium hydroxide (8.1 g) was stirred for 1 hour, while being maintained at 30° C. Then, dimethylsulfuric acid (25.2 g) was dropped at 30° C. over 2 hours. The mixture was stirred at 30° C. for 30 minutes, 40° C. for 2 hours and 50° C. for 4 hours, successively. Then, the same after treatment as in Example 3 was conducted to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (34.9 g, purity 93.7%, yield 91.3%).

Aufarbeitung

  1. stirringThe mixture was stirred at 30° C. for 30 minutes, 40° C. for 2 hours and 50° C. for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-acb0f45d6e68458bb9499c4d64d54769
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017713

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