Triethylamine → N-(3-Methoxyphenyl)-2-methylbenzene-1-carboximidic acid

HRID 1287691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287691
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(N(CC)CC)C.[K+].[Br-]>CCOCC>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH:16][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 702762-Methylbenzoyl chloride2×HCID 253877Potassium Bromide

Produkt 1

HCID 185821N-(3-Methoxyphenyl)-2-methylbenzene-1-carboximidic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A 15.5 g (0.1 mol) portion of o-methylbenzoyl chloride was added dropwise to a stirred solution of 11.9 g (0.1 mol) of m-methoxyaniline and 10.1 g (0.1 mol) of triethylamine in 250 ml of ether and the resulting solution was cooled. After addition of the o-methylbenzoylchloride, the mixture was stirred at room temperature for an additional 5 hours, and the reaction mixture was washed with water to remove triethylamine hydrochloride. The ether layer was dried over anhydrous sodium sulfate and the ether was removed whereby 23.9 g (99%) of fine white prisms having a melting point of 142°-143° C were obtained. IR cm-1 (KBr-tablet), νNH 3250 (S), νCO 1655(S), 1610(S).

Aufarbeitung

  1. temperaturethe resulting solution was cooled
  2. washthe reaction mixture was washed with water
  3. customto remove triethylamine hydrochloride
  4. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  5. customthe ether was removed whereby 23.9 g (99%) of fine white prisms
  6. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-1b195d2e17004dafa89683724a68e3c7
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03985804

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