Captopril → N-(1-Naphthyl)ethylenediamine

HRID 359728

Reaction equation

HRID 359728 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 preparations of S-nitrosocaptopril involve the reaction of 50 mM captopril with 50 mM NaNO2 in 0.1 N 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 were obtained that were

Workup

  1. washthe product eluted with water

Sources & evidence

ORD record
ord-855e4ea735f84408958842a4e014961c
Source dataset
uspto-grants-1991_03
Patent number
US05002964

Linked notes

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