Hydrochloric Acid → N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

HRID 2190363

Reaktionsgleichung

Reaktionsgleichung von HRID 2190363
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:22]=[CH:21][C:11]2[N:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[S:14][C:10]=2[CH:9]=1)([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[CH:22]=[CH:21][C:11]2[N:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[S:14][C:10]=2[CH:9]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 57749256N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 86655349N-[6-(3-aminophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamideAusbeute 108,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of N-[6-(3-nitrophenoxy)-1,3-benzothiazol-2-yl]cyclopropanecarboxamide (840 mg, 2.36 mmol) in ethanol (100 mL) was added iron powder (11.9 g, 212 mmol) with heating under reflux. The obtained suspension was vigorously stirred, and 6N hydrochloric acid (50 mL) was slowly added dropwise. The reaction mixture was refluxed for 2 hr with vigorous stirring, and excess iron powder was filtered off through celite. The filtrate was concentrated to about 50 mL, and the residue was diluted with ethyl acetate (250 mL), washed with 1N aqueous sodium hydroxide solution (100 mLx2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (833 mg) as a pale-yellow solid.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux
  3. filtrationwas filtered off through celite
  4. concentrationThe filtrate was concentrated to about 50 mL
  5. additionthe residue was diluted with ethyl acetate (250 mL)
  6. washwashed with 1N aqueous sodium hydroxide solution (100 mLx2) and saturated brine (100 mL)
  7. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-dfc0d77cedde44388ed4247e39f53fbf
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

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