Ammonium Chloride → HCID 66844939, Verbindung

HRID 2064478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064478
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[O:4].[Cl-].[NH4+]>C(O)C.O.C(Cl)Cl.[Fe]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:4]

Komponenten

7

Edukt 2

HCID 25517Ammonium ChlorideHCID 668446302-Methyl-5-(3-nitrophenyl)thiazole-4-carboxylic acid methyl ester

Produkt 1

HCID 66844939HCID 66844939, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysator3×HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 2-methyl-5-(3-nitro-phenyl)-thiazole-4-carboxylic acid methyl ester (44.1 mmol) and ammonium chloride (220 mmol) in a mixture of ethanol (100 mL) and water (50 mL) is treated with iron powder (53.0 mmol) and heated to 80° C. After 4 h an additional portion of iron powder (53.0 mmol) is added, the mixture is stirred at 80° C. for 3 h, further iron powder (26.5 mmol) is added and the mixture is again stirred at 80° C. for 3.5 h. The mixture is allowed to reach RT, diluted with DCM and filtered through Celite. The filtrate is concentrated in vacuo and diluted with DCM and sat aqueous NaHCO3 solution. The layers are separated and the organic layer is washed with water, dried over MgSO4 and concentrated in vacuo to give the desired aniline derivative. LC-MS: tR=0.67 min; [M+H]+=249.4.

Aufarbeitung

  1. stirringthe mixture is again stirred at 80° C. for 3.5 h
  2. customto reach RT
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. additiondiluted with DCM
  6. customThe layers are separated
  7. washthe organic layer is washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-89f3139eb38e42538c8594c90ffd2a29
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288429B2

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