3-Amino-1,2-propanediol → N1,N3-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamide

HRID 2306142

Reaktionsgleichung

Reaktionsgleichung von HRID 2306142
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16]C)=O)[CH:7]=[C:8]([CH:13]=1)[C:9]([O:11]C)=O)([O-:3])=[O:2].[NH2:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22]>CO>[N+:1]([C:4]1[CH:13]=[C:8]([C:9]([NH:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[O:11])[CH:7]=[C:6]([CH:5]=1)[C:14]([NH:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22])=[O:16])([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 735613-Amino-1,2-propanediolHCID 83316Dimethyl 5-nitroisophthalate

Produkt 1

HCID 11783255N1,N3-Bis(2,3-dihydroxypropyl)-5-nitro-1,3-benzenedicarboxamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Dimethyl 5-nitro-isophthalate and 2.4 molar equivalents of 1-amino-2,3-propanediol were refluxed in methanol for twenty hours and the resulting 5-nitro-N,N′-bis(2,3-dihydroxypropyl)isophthalamide was isolated in 84% yield. The latter compound was suspended in aqueous hydrochloric acid and hydrogenated in the presence of a palladium oxide/charcoal catalyst. The resulting 5-amino-N,N′-bis(2,3-dihydroxypropyl)-isophthalamide was not isolated but the acid solution containing it was iodinated with sodium iodine dichloride to obtain 5-amino-2,4,6-triiodo- N,N′-bis(2,3-dihydroxypropyl)isophthalamide in 71% yield from the nitro compound (over-all yield of 59.5% from dimethyl 5-nitroisophthalate). Subsequent reactions are described for the preparation of 5-[N-(2,3-dihydroxy-propyl)acetamido]-2,4,6 triiodo-N,N′-bis(2,3-dihydroxypropyl)isophthalamide, useful as an X-ray contrast agent.

Quellen und Nachweise

ORD-Eintrag
ord-3d059c5ce8374f5a9eb6bb4b2ebab874
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441235B1

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