Propylenediamine → 2-(1,3-Dimethyl-4-nitropyrazol-5-yl)-4-methylimidazoline

HRID 2417689

Reaktionsgleichung

O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:13][CH2:14][CH:15](N)[CH3:16].[C:18]([C:20]1[N:24]([CH3:25])[N:23]=[C:22]([CH3:26])[C:21]=1[N+:27]([O-:29])=[O:28])#[N:19]>ClC1C=CC=CC=1Cl>[CH3:25][N:24]1[C:20]([C:18]2[NH:13][CH2:14][CH:15]([CH3:16])[N:19]=2)=[C:21]([N+:27]([O-:29])=[O:28])[C:22]([CH3:26])=[N:23]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

p-Toluenesulfonic acid monohydrate (15.2 g, 0.08 mol) is added in portions with stirring to 6 g (0.08 mol) of 1,2-diaminopropane under nitrogen. To the resulting melt (ca 100° C.) is added in portions 12.6 g (0.076 mol) of 5-cyano-1,3-dimethyl-4-nitropyrazole (mp 93° C.); the mixture is stirred and heated to 120° C. and 25 ml of o-dichlorobenzene is added; stirring is continued at 120°-130° for 0.5 hours then at 160° C. for three hours. The cooled mixture is extracted with 75 ml of 3N HCl. The aqueous extract is made strongly basic with a large excess of concentrated NH4OH and the mixture is extracted thoroughly with methylene dichloride. Evaporation of the extract gives 14.3 g (84%) of 2-(1,3-dimethyl-4-nitropyrazol-5-yl)-4-methylimidazoline, mp 98°-101°.

Aufarbeitung

stirringstirring
waitat 160° C. for three hours
extractionThe cooled mixture is extracted with 75 ml of 3N HCl
extractionThe aqueous extract
extractionthe mixture is extracted thoroughly with methylene dichloride
customEvaporation of the extract

Quellen und Nachweise

ORD-Eintrag: ord-98c4bf982f764d9eb1df99f8d49cec75
Quelldatensatz: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04469868

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