Hydrogen Sulfide → HCID 85636719, compound
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- customAfter evaporation the crude product
- customwas purified by chromatography and crystallization from ethyl acetate
Sources & evidence
- ORD record
- ord-4f0d17ddea7b4c5bb615768af629698a
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05179110
Reaction notes
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