Triethylamine → HCID 19088740, Verbindung

HRID 1463840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463840
[S:1]1[C:5]2[C:6]([C:10](Cl)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:13]1([C:19]2([CH2:22][OH:23])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[S:1]1[C:5]2[C:6]([C:10]([O:23][CH2:22][C:19]3([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:20][CH2:21]3)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 5205361-PhenylcyclopropanemethanolHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Produkt 1

HCID 19088740HCID 19088740, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 6.7 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride in 33 ml of dichloromethane is added dropwise at a maximum of 15° C., with cooling, to a solution of 5.0 g of 1-phenylcyclopropanemethanol, 6.1 ml of triethylamine and 200 mg of 4-dimethylaminopyridine in 50 ml of dichloromethane. The mixture is stirred overnight at room temperature until the reaction is complete, dichloromethane and ice-water are added, the aqueous phase is extracted with dichloromethane, and the organic phase is washed with water and NaCl solution, dried over Na2SO4 and concentrated by evaporation. The residue is purified on silica gel (hexane-ethyl acetate 1:1) and the product obtained is recrystallised from diethyl ether/hexane. 7.5 g of crystals having a melting point of 55°-57° C. are obtained.

Aufarbeitung

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. washthe organic phase is washed with water and NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified on silica gel (hexane-ethyl acetate 1:1)
  6. customthe product obtained
  7. customis recrystallised from diethyl ether/hexane
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-e8318fd9277f488a8b946a52083d8fe1
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302607

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