Nitrogen → 4-(4-Amino-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

HRID 2065021

Reaktionsgleichung

Reaktionsgleichung von HRID 2065021
N#N.[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[N:15]2)[N:12]=1)=[O:7])[CH3:4].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([NH2:19])[CH:16]=[N:15]2)[N:12]=1)=[O:7])[CH3:4]

Komponenten

7

Edukt 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 669288954-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

Produkt 1

HCID 669285564-(4-Amino-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 4-(4-nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester (1.77 g, 6.27 mmol), iron powder (1.06 g, 18.81 mmol) and NH4Cl (1.69 g, 31.35 mmol) in a mixture of EtOH (30.0 mL) and water (15.0 mL) was stirred at reflux for 40 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (60 mL) was added followed by 1M NaOH (50 mL). The aq. layer was extracted with CH2Cl2 (2×30 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a brown oil. LC-MS-conditions 02: tR=0.56 min; [M+H]+=253.36.

Aufarbeitung

  1. temperatureat reflux for 40 min
  2. filtrationThe reaction mixture was filtered while hot and
  3. concentrationconcentrated under reduced pressure
  4. additionCH2Cl2 (60 mL) was added
  5. extractionThe aq. layer was extracted with CH2Cl2 (2×30 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1cd0f5df1cb4ce6a66f4d51d53d98bc
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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