Pyridine → 3-[3,4-dichloro-2(5H)-furanon-5-yl]oxy-3-(2-methyl-4-diethylaminophenyl)phthalide

HRID 543348

Reaktionsgleichung

Reaktionsgleichung von HRID 543348
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])=[O:14].S(Cl)(Cl)=O.[C:28]([OH:36])(=[O:35])/[C:29](=[C:31](\[CH:33]=O)/[Cl:32])/[Cl:30].N1C=CC=CC=1>C(Cl)CCl>[Cl:30][C:29]1[C:28](=[O:35])[O:36][CH:33]([O:14][C:13]2([C:3]3[CH:4]=[CH:5][C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:7][C:2]=3[CH3:1])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:19])[O:18]2)[C:31]=1[Cl:32]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 2771871Mucochloric Acid

Produkt 1

HCID 139315013-[3,4-dichloro-2(5H)-furanon-5-yl]oxy-3-(2-methyl-4-diethylaminophenyl)phthalideAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

In a manner similar to that described in Example 1 above, 2.0 g of 2-(2-methyl-4-diethylaminophenyl)carbonylbenzoic acid, 0.77 g of thionyl chloride and 1.1 g of mucochloric acid were interacted in 20.0 ml of ethylene dichloride in the presence of 0.8 ml of pyridine to obtain 2.5 g of 3-[3,4-dichloro-2(5H)-furanon-5-yl]oxy-3-(2-methyl-4-diethylaminophenyl)phthalide (Formula II: R0 =R=R1 =R2 =H; R4 =R4' =R5 =CH3 ; X=O; Y=3,4-dichloro-2-(5H)-furanon-5-yl), an orange-colored oil. A significant infrared maximum appeared at 1758 cm-1 (C=O;s). A toluene solution of the product spotted on an acidic clay-coated paper developed a yellow-colored image.

Quellen und Nachweise

ORD-Eintrag
ord-12daeb36a2974bd8ac256cd3807a0b2b
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661605

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