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

HRID 2051382

Reaktionsgleichung

Reaktionsgleichung von HRID 2051382
[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.Cl[C:23]1C=CC=CC=1.[OH-].[K+].CCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[K+].C(O)(=O)C.O>[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]([CH3:23])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

Komponenten

9

Edukt 4

HCID 6327Methyl ChlorideHCID 7964ChlorobenzeneHCID 14797Potassium 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 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 4875Potassium IodideKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

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), 96% potassium hydroxide (12.0 g) and potassium iodide (0.5 g) was stirred for 1 hour in an autoclave, while being maintained at 30° C. Then, methyl chloride (10.2 g) was added. The mixture was stirred at 50° C. for 2 hours and 70° C. for 10 hours, successively. After the temperature was lowered to 30° C. and pressure was released, the solution was transferred to a flask by adding water (200 g), and then acetic acid (1.2 g) was added thereto. The aqueous phase had pH of 7. After monochlorobenzene was recovered by heating, the solution was cooled down to 50° C. and filtered. The solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (34.7 g, purity 92.9%, yield 90.0%).

Aufarbeitung

  1. stirringThe mixture was stirred at 50° C. for 2 hours and 70° C. for 10 hours
  2. customwas lowered to 30° C.
  3. customthe solution was transferred to a flask
  4. customAfter monochlorobenzene was recovered
  5. temperatureby heating
  6. temperaturethe solution was cooled down to 50° C.
  7. filtrationfiltered
  8. washThe solid material was washed
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f7f17469e4a945f98377f36a08edbf51
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017713

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