Hydrogen Sulfide → HCID 85636719, 화합물

HRID 1646226노트

반응식

HRID 1646226 반응식
[NH2:1][C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:3][C:4]#[N:5].[SH2:12]>N1C=CC=CC=1.C(N(CC)CC)C>[NH2:1][C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:3][C:4](=[S:12])[NH2:5]

참가 물질

5

반응물 2

HCID 402Hydrogen Sulfide2회HCID 692825693-Amino-3-(pyridin-3-yl)prop-2-enenitrile

생성물 1

HCID 85636719HCID 85636719, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8471Triethylamine용매

실험 절차

A solution of 20 g of 3-amino-3-(3-pyridinyl)-2-propenenitrile [J. Med. Chem., 18, 441 (1975)] in 100 ml of pyridine and 14 ml of triethylamine was saturated with hydrogen sulfide and set aside under nitrogen at room temperature for 28 days. The solution was kept saturated by passing hydrogen sulfide into the reaction mixture at intervals during this time. After evaporation the crude product was purified by chromatography and crystallization from ethyl acetate to give 3.65 g of 3-amino-3-(3-pyridinyl)-2-propenethioamide, which was suspended in 80 ml of diethyl ether together with 5.21 g of potassium carbonate. A solution of 5.21 g of iodine in 80 ml of diethyl ether was added dropwise in 10 min to this suspension, keeping the temperature at 3±2° C. After 45 min the reaction mixture was diluted with brine and extracted with dichloromethane. The extract was washed, dried, and evaporated to give 2.19 g of 3-(3-pyridinyl)-5-isothiazolamine.

후처리

  1. customAfter evaporation the crude product
  2. customwas purified by chromatography and crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-4f0d17ddea7b4c5bb615768af629698a
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05179110

반응 노트

불러오는 중…