Captopril → N-(1-Naphthyl)ethylenediamine

HRID 2082051Notes

Reaction equation

HRID 2082051 reaction equation
C[C@@H:2]([C:7]([N:9]1[C@H:13]([C:14](O)=O)[CH2:12][CH2:11][CH2:10]1)=O)CSN=O.C[C@@H](C(N1[C@H:27]([C:28](O)=O)[CH2:26][CH2:25][CH2:24]1)=O)CS.[N:31]([O-])=O.[Na+]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.S(=O)(=O)(O)O>[C:13]1([NH:9][CH2:7][CH2:2][NH2:31])[C:14]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 44093CaptoprilHCID 129596S-NitrosocaptoprilHCID 23668193Sodium Nitrite

Product 1

HCID 15107N-(1-Naphthyl)ethylenediamine

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

Typical preparation of S-nitrosocaptopril involve the reaction of 50 mM captopril with 50 mM NaNO2 in 0.1N acetic or sulfuric acid at room temperature for five minutes, after which the reaction solution is passed over a cation exchange resin, e.g., Dowex 50 in the protonated form, and the product eluted with water. The fractions that give positive reactions with N-(1-naphthyl)ethylenediamine, after exposure to 0.15% HgCl2 and diazotization with sulfanilamide, are lyophilized. Hygroscopic, bright red crystals (m.p. 98°-104° C.) were obtained that were shown to be S-nitrosocaptopril by NMR in deuterated DMSO and by mass spectroscopy.

Workup

  1. washthe product eluted with water

Sources & evidence

ORD record
ord-6a86bab0093544ccbf57c23e61584faa
Source dataset
uspto-grants-1993_02
Patent number
US05187183

Reaction notes

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