Sodium Iodide → methyl 3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH2:13][CH2:14]Cl)[C:5]([O:7][CH3:8])=[O:6].[I-].[Na+]>CC(=O)CC>[S:12]1[CH2:13][CH2:14][NH:1][C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of methyl 3-amino-4-(2-chloroethylthio)benzoate (19.7 mg, 0.080 mmol) in 2-butanone (2 mL) was added sodium iodide (36 mg, 0.240 mmol). The reaction mixture was heated to 70° C. and stirred over night at that temperature. The reaction mixture was cooled to room temperature. TLC and LCMS analysis of the reaction mixture indicated product formation. The product was purified by flash column chromatography [gradient elution with Hexanes and 5-50% EtOAc]. To provide methyl 3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxylate (8.6 mg, 0.040 mmol, 49.6% overall 3 steps) as an off-white solid.