Hydrochloric Acid → N-(p-azidobenzenesulfonyl) N'-(3-carboxypropionyl) cystamine

HRID 1603190

Reaktionsgleichung

Reaktionsgleichung von HRID 1603190
Cl.Cl.NCCSSCCN.[OH-].[Na+].[N:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][S:28][S:29][CH2:30][CH2:31][NH:32][C:33](=[O:46])[CH2:34][CH2:35][C:36]([O:38]N2C(=O)CCC2=O)=[O:37])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[N+:14]=[N-:15].C1(=O)OC(=O)CC1.Cl>O>[N:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][CH2:27][S:28][S:29][CH2:30][CH2:31][NH:32][C:33](=[O:46])[CH2:34][CH2:35][C:36]([OH:38])=[O:37])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[N+:14]=[N-:15]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5941Cystamine DihydrochlorideHCID 7922Succinic anhydrideHCID 14798Sodium HydroxideHCID 19609028HCID 19609028, Verbindung

Produkt 1

HCID 19609019N-(p-azidobenzenesulfonyl) N'-(3-carboxypropionyl) cystamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2.2 g of cystamine dihydrochloride were dissolved in 20 ml of water and adjusted to pH 10 with NaOH. 2.1 g of p-azidobenzenesulfochloride were suspended in the solution and the mixture was stirred at room temperature for 5 hours. The precipitated N-(p-azidobenzenesulfonyl)cystamine was reacted with 2 g of succinic anhydride and stirred overnight. The resulting solution was acidified with HCl and the product was subsequently filtered off and washed with water. The residue was dried at room temperature in a high vacuum and gave 1.53 g of N-(p-azidobenzenesulfonyl)-N'-(3-carboxypropionyl)cystamine. The IR showed bands at 3283 (amide NH), 2134 (azide), 1714 (acid carbonyl), 1650 (amide), 1589+1547 (aromatic), 1284 (COOH), 1328+1180 (arylsulfonyl), 839 (p- disubst. benzene); TLC (silica gel: conc. NH3 (EtOH=1%). Rf=0.7; m.p. 163° (dec.).

Aufarbeitung

  1. stirringstirred overnight
  2. filtrationthe product was subsequently filtered off
  3. washwashed with water
  4. customThe residue was dried at room temperature in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1098af0e084b48738a80de62db0fe224
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986066

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