Ammonia → 7-Fluoro-1,3-benzothiazol-2-amine
Reaction equation
[F:1][C:2]1[C:10]2[S:9][C:8](S(C)(=O)=O)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH3:15]>C(O)C>[NH2:15][C:8]1[S:9][C:10]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
A mixture of 7-fluoro-2-methylsulfonyl-1,3-benzothiazole (500 mg, 2.16 mmol) in 10 mL ethanol and 20% ethanolic ammonia (20 mL) was heated at 160° C. in a sealed tube for 12 h. It was cooled to RT, ethanol was removed under reduced pressure, and the brownish residue was purified by column chromatography (5% to 10% methanol in methylene chloride) to afford the title compound. 1H-NMR (CDCl3, 300 MHz): δ=7.35 (d, J=7.5 Hz, 1H), 7.33-7.37 (m, 1H), 6.93-6.84 (m, 1H), 5.30 (brs, 2H).
Workup
- temperatureIt was cooled to RT
- customethanol was removed under reduced pressure
- customthe brownish residue was purified by column chromatography (5% to 10% methanol in methylene chloride)
Sources & evidence
- ORD record
- ord-fbd7008f0aec4d6c826646992077952a
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178668B2
Reaction notes
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