Tetrahydrofuran → Benzo-1,2,3-thiadiazol-7-yl-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 6361

Reaktionsgleichung

Reaktionsgleichung von HRID 6361
[S:1]1[C:5]2[C:6](C(Cl)=O)=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:13]([O-:19])(=[O:18])[CH2:14][C:15]([O-:17])=[O:16].C(N(CC)CC)C.O1C[CH2:30][CH2:29][CH2:28]1>CN(C)C1C=CN=CC=1.ClCCl>[S:1]1[C:5]2[C:6]([CH:14]3[C:13](=[O:19])[O:18][C:29]([CH3:30])([CH3:28])[O:16][C:15]3=[O:17])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9084Malonate IonHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Produkt 1

HCID 86747249Benzo-1,2,3-thiadiazol-7-yl-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.5 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 10 ml of tetrahydrofuran are added dropwise to a solution, stirred at 0° C., of 3.6 g of cycloisopropylidene malonate, 7.6 ml of triethylamine and 2.0 g of 4-dimethylaminopyridine in 25 ml of dichloromethane. The reaction mixture is stirred for 2 hours at 0° C. and then applied directly to a silica gel column and extracted with ethyl acetate, resulting in the title compound in the form of a salt with 4-dimethylaminopyridine (2:1), m.p. 170°-172° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-48b492e5913b4918978d9c22b2beb223
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248683

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