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Sulfuric Acid → 2-Amino-2-(4-chloro-2-fluoro-5-methoxyphenyl)acetamide

HRID 849966
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 849966
S(=O)(=O)(O)O.[NH2:6][CH:7]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([Cl:18])=[CH:12][C:11]=1[F:19])[C:8]#[N:9].[OH2:20].N>O>[NH2:6][CH:7]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([Cl:18])=[CH:12][C:11]=1[F:19])[C:8]([NH2:9])=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 12896473Azane;hydrateHCID 193654932-Amino-2-(4-chloro-2-fluoro-5-methoxyphenyl)acetonitrile

Produkt 1

HCID 193655102-Amino-2-(4-chloro-2-fluoro-5-methoxyphenyl)acetamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Then, 3.6 g of concentrated sulfuric acid was added to 0.33 g of water, to which 3.6 g of 2-amino-2-(4-chloro-2-fluoro-5-methoxyphenyl)acetonitrile was added under ice cooling, and the mixture was heated at 50° to 60° C. under stirring for 3 hours. After completion of the reaction, the reaction mixture was poured into 15 ml of concentrated ammonia water cooled with ice in such a manner that the temperature of the solution became not higher than 20° C. The precipitated crystals were collected by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was combined with the previously collected crystals, followed by recrystallization, which afforded 2.45 g (yield, 68%) of 2-amino-2-(4-chloro-2-fluoro-5-methoxyphenyl)acetamide, m.p. 161.7° C.

Aufarbeitung

  1. additionwas added under ice cooling
  2. temperaturethe mixture was heated at 50° to 60° C.
  3. customAfter completion of the reaction
  4. temperaturecooled with ice in such a manner that the temperature of the solution
  5. custombecame not higher than 20° C
  6. filtrationThe precipitated crystals were collected by filtration
  7. extractionthe filtrate was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated sodium chloride solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customfollowed by recrystallization, which

Quellen und Nachweise

ORD-Eintrag
ord-7d254c2544894bbab1e82a9a46c53f1a
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06015774

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