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Hydrochloric Acid → Diethyl 2-(benzo-1,2,3-thiadiazol-7-yl)malonate

HRID 6362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 6362
[Cl-].[Mg+2].[Cl-].[C:4]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[S:15]1[C:19]2[C:20](C(Cl)=O)=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1.Cl>C(#N)C.C(N(CC)CC)C>[S:15]1[C:19]2[C:20]([CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]([O:12][CH2:13][CH3:14])=[O:11])=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360315Magnesium ChlorideHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Produkt 1

HCID 19793424Diethyl 2-(benzo-1,2,3-thiadiazol-7-yl)malonateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342
Acetonitrile
Lösungsmittel
2×
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4.8 g of magnesium chloride in 50 ml of acetonitrile are treated with 7.6 ml of diethyl malonate and 14 ml of triethylamine, with ice-cooling and stirring. The mixture is stirred for 20 minutes and then treated at 0°-5° C. with portions of a suspension of 9.6 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 50 ml of acetonitrile, the temperature being maintained at between 5° C. and 15° C. The resulting beige suspension is stirred for a further hour in an ice-bath at 0° C. and subsequently overnight at room temperature. On the next day, it is cooled again to 0° C., brought to pH 4.5 using 15% hydrochloric acid, and extracted with ethyl acetate. The extracts are dried over sodium sulfate, filtered over silica gel and evaporated. This results in the title compound in a yield of 83.2% of theory and with a melting point of 72°-74° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture is stirred for 20 minutes
  3. temperaturethe temperature being maintained at between 5° C. and 15° C
  4. stirringThe resulting beige suspension is stirred for a further hour in an ice-bath at 0° C. and subsequently overnight at room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts are dried over sodium sulfate
  7. filtrationfiltered over silica gel
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ac19de6fdddf43cb807f1b8ce12dad02
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05248683

Notizen zur Reaktion

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