Sulfuric Acid → 4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

HRID 1362972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362972
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11]C(=O)C)=[CH:7][C:6]=1[C:15]1[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=1.S(=O)(=O)(O)O>CO>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:15]1[N:16]([CH3:20])[N:17]=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 58964265N-[4-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide

Produkt 1

HCID 468336804-(2-bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenylamineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of N-[4-(2-Bromo-ethoxy)-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide (3 g, 8.9 mmole) in methanol (6 mL) was added Sulfuric acid (2.2 mL, 42 mmole, 4.78 eq) at 0° C. while stirring. The reaction mixture was refluxed at 90° C. for 1 hour 20 minutes. Crude was quenched with water, neutralized with saturated sodium hydroxide solution until pH 8, extracted with ethyl acetate, and then concentrated in vacuo to give title compound as a solid (2.6 g, 99%). Exact mass calculated for C12H14BrN3O 295.0. found 296.1 (M+H 79Br, 100), 298.2 (M+H 81Br, 98).

Aufarbeitung

  1. customCrude was quenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-736b65aa12874cf4927983c7d95e8f88
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884101B2

Notizen zur Reaktion

Wird geladen…