Hydrogen Sulfide → HCID 85636719、化合物

HRID 1646226ノート

反応式

HRID 1646226 の反応式
[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]

参加物

5

反応物 2

HCID 402Hydrogen Sulfide2 回HCID 692825693-Amino-3-(pyridin-3-yl)prop-2-enenitrile

生成物 1

HCID 85636719HCID 85636719、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4f0d17ddea7b4c5bb615768af629698a
出典データセット
uspto-grants-1993_01
特許番号
US05179110

反応ノート

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