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

HRID 6361

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-48b492e5913b4918978d9c22b2beb223
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05248683

Linked notes

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