Ammonia → n-Propoxybenzamidine methyl sulfate

HRID 2082712

Reaktionsgleichung

Reaktionsgleichung von HRID 2082712
[CH3:1][O:2][S:3]([OH:6])(=[O:5])=[O:4].[CH2:7]([O:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13](=[NH:16])OC)[CH2:8][CH3:9].[NH3:21]>C(O)C>[CH3:1][O:2][S:3]([OH:6])(=[O:5])=[O:4].[CH2:7]([O:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH2:21])=[NH:16])[CH2:8][CH3:9]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 86735597Methyl 2-n-propoxybenzimidate methyl sulfate

Produkt 1

HCID 86734867n-Propoxybenzamidine methyl sulfateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a warm, stirred solution of 2-n-propoxybenzamide (896 g., 5.0 moles) in 1,2-dichloroethane (5 l) was added dimethyl sulfate (950 ml., 10.0 moles) over a period of about 0.5 hour. The mixture was stirred and heated under reflux for 17 hours. The solvent was removed. The residual oily solid was collected by filtration, washed with ethyl acetate and dried to give methyl 2-n-propoxybenzimidate methyl sulfate (403 g.), m.p. 79°-82°. The combined filtrate and washings were stored at 0° for 18 hours and gave a second crop (503 g.) of benzimidate, m.p. 81°-83°. A slurry of the methyl 2-n-propoxybenzimidate methyl sulfate (906 g.) in ethanol (1 l) was added to ethanol ( 4 l) which had previously been saturated with gaseous ammonia. The mixture was stored at room temperature for 17 hours. The mixture was filtered. The filtrate was evaporated to dryness to give 2-n-propoxybenzamidine methyl sulfate (872 g., 60%), m.p. 86°-88°.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e062777e0e5245c9bd927f99545a8aa8
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04082751

Verknüpfte Notizen

Wird geladen…