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Methyl chloroformate → HCID 56973781, Verbindung

HRID 1833831
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1833831
[CH3:1][O:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[C:13]([NH:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=1)([CH3:16])([CH3:15])[CH3:14]>CC(C)=O>[C:13]([NH:17][C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:3]([O:2][CH3:1])=[O:4])[CH:21]=1)([CH3:16])([CH3:14])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 28689665HCID 28689665, Verbindung

Produkt 1

HCID 56973781HCID 56973781, VerbindungAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
17.5 °C

Versuchsvorschrift

10.45 g (0.1 mol) of chloroformic acid methyl ester, followed by 10.1 g (0.1 mol) of triethylamine, were added dropwise to a solution of 20.6 g (0.1 mol) of 3-amino-phenylacetic acid tert.-butylamide in 200 ml of acetone whilst cooling at 15 to 20° C. The mixture was stirred for a further 2 hours at room temperature, the triethylamine hydrochloride which had precipitated was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue which hereupon remained was stirred with very dilute hydrochloric acid, filtered off, dried and recrystallized from a little carbon tetrachloride. 22 g (83.5% of theory) of 3-methoxycarbonylamino-phenylacetic acid tert.-butylamide of melting point 123°-124° C were obtained.

Aufarbeitung

  1. customthe triethylamine hydrochloride which had precipitated
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. stirringThe residue which hereupon remained was stirred with very dilute hydrochloric acid
  5. filtrationfiltered off
  6. customdried
  7. customrecrystallized from a little carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-43487cc559164cc490c9b6dcefb93e70
Quelldatensatz
uspto-grants-1978_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04067726

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