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Trifluoroacetic acid → 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

HRID 871002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 871002
[Cl:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[S:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:5]2[S:4][N:3]=[C:2]([Cl:1])[C:6]=2[C:7]#[N:8])=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86689222tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate

Produkt 1

HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate (4.76 g, 13.38 mmol) in DCM (100 ml) was treated with 10 mL of TFA. The reaction mixture was stirred at RT overnight. Solvent was removed in vacuo. The residue was diluted with water and DCM (100 ml). Layers were separated and the aqueous layer was extracted with DCM×2. The combined organics was washed with brine and dried with MgSO4, filtered, and concentrated. Product was rinsed with Et2O/hexanes and collected by filtration as a bright yellow solid (3.15 g, 94%).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. additionThe residue was diluted with water and DCM (100 ml)
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with DCM×2
  5. washThe combined organics was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washProduct was rinsed with Et2O/hexanes
  10. filtrationcollected by filtration as a bright yellow solid (3.15 g, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-e139ca9805d64efcb72214d9a8de634b
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969583B2

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