Potassium Hydroxide → 3-Ethoxycarbonyl-1H-pyrido[2,3-b][1,4]-thiazine
Reaction equation
Cl[CH:2]([CH:8]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[SH:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=1.[OH-].[K+]>C(O)C>[CH2:6]([O:5][C:3]([C:2]1[S:10][C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:16]=2[NH:17][CH:8]=1)=[O:4])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
4.8 g of ethyl α-chloro-formylacetate, dissolved in 70 ml of ethanol, are added to a solution of 4 g (0.0317 mole) of 2-mercapto-3-aminopyridine and 1.78 g (0.0317 mole) of potassium hydroxide in 200 ml of ethanol at 25° C. under nitrogen. The mixture is warmed at 50° C. for 1 hour, the ethanol is then stripped off in vacuo and the residue is chromatographed on silica gel with methylene chloride/methanol (95:5) as the mobile phase. Yield: 3.3 g (47% of theory) Melting point: 194°-195° C.
Workup
- customthe residue is chromatographed on silica gel with methylene chloride/methanol (95:5) as the mobile phase
Sources & evidence
- ORD record
- ord-bf71ee591e9e4476afa5098d859367be
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04861878
Reaction notes
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