Chloral alcoholate → N-(4-bromo-2-methoxyphenyl)-2-(hydroxyimino)acetamide

HRID 1052980

Reaktionsgleichung

Reaktionsgleichung von HRID 1052980
Cl.[NH2:2][OH:3].Cl[C:5](Cl)(Cl)[CH:6]([O:8]CC)O.S([O-])([O-])(=O)=O.[Na+].[Na+].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([O:28][CH3:29])[CH:22]=1>O.Cl>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:6](=[O:8])[CH:5]=[N:2][OH:3])=[C:23]([O:28][CH3:29])[CH:22]=1

Komponenten

7

Edukt 4

HCID 10587Chloral alcoholateHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 4592574-Bromo-2-methoxyaniline

Produkt 1

HCID 117668132N-(4-bromo-2-methoxyphenyl)-2-(hydroxyimino)acetamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Hydroxylamine hydrochloride (6.67 g, 96 mmol) in water (15 mL) was added to a suspension of 2,2,2-trichloro-1-ethoxyethanol (6.96 g, 36 mmol) and sodium sulfate (38.3 g, 270 mmol) in water (45 mL) and 2N HCl (30 mL). The mixture was stirred at 60° C. for 20 min. 4-Bromo-2-methoxybenzenamine (6.06 g, 30 mol) in 2N HCl (30 mL) was added, and the mixture was heated to 90° C. for 2 h. The mixture was cooled to room temperature. The solid was collected by filtration, washed with water, and air dried to afford the title compound (5.55 g, crude, 68% yield). This material was used in the next step without further purification. MS (ESI) m/e [M+1]+ 273, 275.

Aufarbeitung

  1. temperaturethe mixture was heated to 90° C. for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, and air
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-93b3f8b4e035460eaa558faf2692cc4c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393232B2

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