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Hydrochloric Acid → 5-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

HRID 2227567
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2227567
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21](Cl)=[O:22])([CH3:15])([CH3:14])[CH3:13].Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21]([NH:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:22])([CH3:15])([CH3:13])[CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4657O-Methyltyramine2×HCID 221431005-Tert-butyl-2-methoxybenzoyl chloride

Produkt 1

HCID 184743175-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

1.51 g (10.0 mmol) of 2-(4-methoxyphenyl)ethylamine were dissolved in 40 ml of pyridine and admixed with a spatula tip of 4-dimethylaminopyridine and then with a solution of 2.15 g (10.5 mmol) of 5-tert-butyl-2-methoxybenzoyl chloride. After the 2-(4-methoxyphenyl)ethylamine had been converted completely, the reaction mixture was poured into cold dilute hydrochloric acid, and the precipitated product was filtered off with suction and dried to give 5-tert-butyl-2-methoxy-N-[2-(4-methoxyphenyl)ethyl]benzamide as a colorless solid. The benzamide was introduced into cold chlorosulfonic acid. After the benzamide had been converted completely, the reaction mixture was poured onto ice and filtered off with suction, and the precipitate was dissolved in acetone. This solution was admixed with excess concentrated aqueous ammonia. After the exothermic reaction had subsided, the mixture was concentrated to a third of its original volume and the precipitate was filtered off with suction. The 5-[2-(5-tert-butyl-2-methoxybenzamido)ethyl]-2-methoxybenzenesulfonamide was obtained in the form of colorless crystals of melting point 165-168° C.

Aufarbeitung

  1. filtrationthe precipitated product was filtered off with suction
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-88fe54cdfec5442eadca15b57e02238c
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06414030B1

Notizen zur Reaktion

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