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Dimethyl Sulfoxide → 4'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

HRID 462555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 462555
[CH3:1][S:2]([CH3:5])(=[O:4])=[O:3].[H-].[Na+].CS(C)=O.C[O:13][C:14](=O)[C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([NH2:22])=[C:17]([CH3:23])[CH:16]=1>C(O)(=O)C.O>[NH2:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([C:14](=[O:13])[CH2:1][S:2]([CH3:5])(=[O:4])=[O:3])=[CH:16][C:17]=1[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6213Dimethyl SulfoneHCID 24758Sodium hydrideHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

Produkt 1

HCID 212810124'-Amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 33 g. of dimethylsulfone and 11 g. of sodium hydride (50% dispersion in oil) in 160 ml. of absolute dimethylsulfoxide was stirred at 50° C. under an atmosphere of nitrogen and the exclusion of moisture for 3 hours. Then, 18 g. of 4-amino-3,5-dimethyl-benzoic acid methyl ester were added. The mixture was stirred at 80° C. for 30 minutes and at room temperature for 1 hour and then dissolved in 400 ml. of water. The solution was neutralized with glacial acetic acid. The precipitate which formed was removed by filtration with suction, washed with water, dried and recrystallized from ethyl acetate, whereby there was obtained 4'-amino-3',5'-dimethyl-2-(methylsulfonyl)-acetophenone having a melting point of 179°-180° C.

Aufarbeitung

  1. additionA suspension of 33 g
  2. dissolutiondissolved in 400 ml
  3. customThe precipitate which formed
  4. customwas removed by filtration with suction
  5. washwashed with water
  6. customdried
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5d2d7edd105b48e1a0e03c2ab17533c7
Quelldatensatz
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04515948

Notizen zur Reaktion

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