Water → 2,3-Dihydro-1,4-benzothiazine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH2:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[S:8]1[CH2:11][CH2:10][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-aminothiophenol (5 g, 40 mmol), 1,2-dibromoethane (3.75 g, 20 mmol), K2CO3 (13.8 g, 100 mmol) in THF (30 mL) was heated at 100° C. for 16 h. After completion of reaction, water was added and extracted with EtOAc. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The reaction mixture was purified by column chromatography (using 100-200 mesh silica) and the desired product was eluted at 15% EtOAc in hexane) to obtained 2.2 g of desired product.
Workup
- additionwas added
- extractionextracted with EtOAc
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe reaction mixture was purified by column chromatography (using 100-200 mesh silica)
- washthe desired product was eluted at 15% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-102b3bdccbfb4b1da314f35914be9e99
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193728B2
Reaction notes
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