Captopril → N-(1-Naphthyl)ethylenediamine

HRID 1707947

반응식

HRID 1707947 반응식
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

참가 물질

6

반응물 3

HCID 44093CaptoprilHCID 129596S-NitrosocaptoprilHCID 23668193Sodium Nitrite

생성물 1

HCID 15107N-(1-Naphthyl)ethylenediamine

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester용매

실험 절차

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.

후처리

  1. washthe product eluted with water

출처 및 근거

ORD 기록
ord-dd03f2d1929c4906a123337dd8a492fe
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356890

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