Methanol → 3-Methoxy-3-(4-dimethylaminophenyl)phthalide

HRID 485114

Reaktionsgleichung

Reaktionsgleichung von HRID 485114
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.CO.N1CCCC[CH2:28]1>C(Cl)CCl>[CH3:28][O:10][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:20])[CH3:1])=[CH:8][CH:7]=2)[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13](=[O:15])[O:14]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 889372-[4-(Dimethylamino)benzoyl]benzoic acid

Produkt 1

HCID 159186993-Methoxy-3-(4-dimethylaminophenyl)phthalide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Following a procedure similar to that described in Example 1 above, 4.5 g of 2-(4-dimethylaminophenyl)carbonylbenzoic acid, 1.2 ml of thionyl chloride and 5.0 ml of methyl alcohol were interacted in 30.0 of ethylene dichloride in the presence of 1.3 ml of piperidine at ambient temperature for approximately ten minutes to obtain 4.0 g of 3-methoxy-3-(4-dimethylaminophenyl)phthalide (Formula II: R0 =R=R1 =R2 =R5 =H; R4 =R4' =R5 =Y=CH3 ; X=O), a pale peach-colored solid which melted at 112.5° to 114.5° C. A significant infrared maximum appeared at 1773 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Analysis by mass spectrum showed m/e peaks at 283 (M+) and 252 (M+ --OCH3). A toluene solution of the product spotted on an acidic clay-coated paper developed a yellor-colored image.

Quellen und Nachweise

ORD-Eintrag
ord-fd7721f72b334464b1242b712dc349ac
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04535172

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