Dicyclohexylamine → 4-But-2-ynyloxybenzoyl chloride

HRID 517488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517488
C1(NC2CCCCC2)CCCCC1.[CH2:14]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)[C:15]#[C:16][CH3:17].S(Cl)([Cl:30])=O>ClCCl>[CH2:14]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:30])=[O:24])=[CH:21][CH:20]=1)[C:15]#[C:16][CH3:17]

Komponenten

5

Edukt 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 222825564-But-2-ynyloxy-benzoic acid

Produkt 1

HCID 593240144-But-2-ynyloxybenzoyl chlorideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.8 ml (14.2 mmol) of dicyclohexylamine are added to a solution of 2.7 g (14.2 mmol) of 4-but-2-ynyloxybenzoic acid diluted in 30 ml of dichloromethane. After stirring for 30 min at ambient temperature, the reaction medium is cooled to 0° C. and 1.0 ml (14.2 mmol) of thionyl chloride is slowly added. The mixture is then stirred at ambient temperature for 1 h 30 min, then the dicyclohexylamine salts are precipitated by adding 50 ml of diethyl ether. After filtration of the reaction medium, the filtrate is concentrated under vacuum. 2.9 g (100%) of 4-but-2-ynyloxybenzoyl chloride are obtained in the form of a brown solid.

Aufarbeitung

  1. temperaturethe reaction medium is cooled to 0° C.
  2. stirringThe mixture is then stirred at ambient temperature for 1 h 30 min
  3. customthe dicyclohexylamine salts are precipitated
  4. additionby adding 50 ml of diethyl ether
  5. filtrationAfter filtration of the reaction medium
  6. concentrationthe filtrate is concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-29f7082b7c774bd0838ef479228189b9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115102B2

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