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

HRID 2051377

Reaktionsgleichung

Reaktionsgleichung von HRID 2051377
[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-].[K+].[CH3:24]OS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.ClC1C=CC=CC=1.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]([CH3:24])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 6497Dimethyl SulfateHCID 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 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittel2×

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 96% potassium hydroxide (12.0 g) was stirred for one hour while being maintained at 30° C. 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. After water (200 g) was added, the solution was stirred for 1 hour while being maintained at 50° C. pH of the aqueous phase was 10 or higher. After acetic acid (0.5 g) was added for neutralization (pH of the aqueous phase being 7), monochlorobenzene was recovered by heating. After being cooled down to 50° C., the solution was filtered. A solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (35.0 g, purity 94.0%, yield 91.9%).

Aufarbeitung

  1. stirringThe mixture was stirred at 30° C. for 30 minutes, 40° C. for 2 hours and 50° C. for 4 hours
  2. stirringthe solution was stirred for 1 hour
  3. temperaturewhile being maintained at 50° C. pH of the aqueous phase
  4. customwas recovered
  5. temperatureby heating
  6. temperatureAfter being cooled down to 50° C.
  7. filtrationthe solution was filtered
  8. washA solid material was washed
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d04364ea92af4144b57991ed197505f3
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017713

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