1,3-Propanediamine → Drometrizole

HRID 27259

Reaktionsgleichung

Reaktionsgleichung von HRID 27259
NCCCN.O.[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[N:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[OH:25])([O-])=O>C1(C)C(C)=CC=CC=1.[Cu].II.CC(O)=O>[OH:25][C:19]1[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=1[N:17]1[N:16]=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[N:7]1

Komponenten

6

Edukt 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenol

Produkt 1

HCID 17113Drometrizole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131711869copper II-acetateKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

11.6 g of 1,3-diaminopropane (0.16 mol) and 2 g of copper-II-acetate (0.01 mol) are placed into 50 ml of water and the whole is heated, with the exclusion of air and with stirring, to 85°-90° C. A solution of 10 g of 2-nitro-2'-hydroxy-5'-methyl-azobenzene (0.04 mol) in 100 ml of xylene heated to 60° C. is then added, and after 20 hours the reaction mixture is cooled to room temperature. The aqueous phase is separated, and the organic phase is extracted with aqueous hydrochloric acid, and then washed with water until neutral. The xylene is distilled off to leave 7.7 g of crude product. Analysis of the crude product by means of LC (liquid chromatography) gives 86% of theory of 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole.

Aufarbeitung

  1. temperaturethe whole is heated, with the exclusion of air
  2. additionis then added
  3. customThe aqueous phase is separated
  4. extractionthe organic phase is extracted with aqueous hydrochloric acid
  5. washwashed with water until neutral
  6. distillationThe xylene is distilled off
  7. customto leave 7.7 g of crude product

Quellen und Nachweise

ORD-Eintrag
ord-8705d867eebf45b3a038ae1dfffdf136
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220788

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