1,2-Dichlorobenzene → p-Toluenesulfonic acid

HRID 66771

Reaktionsgleichung

Reaktionsgleichung von HRID 66771
CSC1C=CC(C)=CC=1OCC1NCCN=1.CSC1C=CC(C)=CC=1OCC#N.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1.C(N)CN.ClC1C=CC=CC=1Cl>C(Cl)Cl>[CH3:40][C:30]1[CH:35]=[CH:34][C:33]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 72391,2-DichlorobenzeneHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 705471844-Methylthio-m-tolyloxyacetonitrileHCID 705477522-((4-(Methylthio)-m-tolyloxy)methyl)-2-imidazoline

Produkt 1

HCID 6101p-Toluenesulfonic acidAusbeute 188,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The product, 2-((4-(methylthio)-m-tolyloxy)methyl)-2-imidazoline, was prepared by heating 19.3 g of 4-methylthio-m-tolyloxyacetonitrile, 23.3 g of ethylenediamine p-toluenesulfonate and 75 ml of 1,2-dichlorobenzene substantially as described in previous examples. Upon cooling the reaction mixture, diluting with CH2Cl2 and filtering, 32.5 g of p-toluenesulfonate salt was obtained. The p-toluenesulfonate salt was then slurried in water and CH2Cl2 and then basified. The CH2Cl2 layer was separated and the aqueous layer extracted with chloroform. The extracts were combined, treated with diatomaceous earth and activated charcoal and then filtered. The filtrate was taken to dryness, which gave 13.5 g of the product, 2-((4-(methylthio)-m-tolyloxy)methyl)-2-imidazoline as a white solid, m.p. 102°-104° C.

Aufarbeitung

  1. temperatureUpon cooling the reaction mixture
  2. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-9f359e437e9c4394970d53471b23e6ed
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343808

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