Sodium Chloride → HCID 19754260, compound
Reaction equation
C(N(CC)CC)C.B(F)(F)F.[C:12]([C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:18]=2[CH:19]=1)(=O)[CH3:13].[Cl-].[Na+]>ClCCl>[CH2:12]([C:15]1[S:16][C:17]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:18]=2[CH:19]=1)[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 22.6 g (0.195 mole) of triethylamine in 50 ml of dichloromethane is cooled to 0° C. by means of an ice-sodium chloride bath. Boron trifluoride is then added to saturate the solution (about 25 g). A solution of 14.4 g (0.065 mole) of 2-acetyl 5-nitro benzothiophene in 50 ml of dichloromethane is added while the temperature is maintained at 0° C. Stirring is continued at 0° C. for 0.5 h while a very gentle stream of boron trifluoride is introduced. The complex formed is decomposed with a saturated solution of sodium chloride, the organic fraction is washed three times with a solution of sodium chloride and dried over anhydrous sodium sulfate. It is filtered and the solvent is evaporated at a rotary evaporator. In this manner, 16.6 g of 2-ethyl 5-nitro benzothiophene are obtained in the form of a yellow solid which is purified by chromatography on a column of silica (eluant: heptane/ethyl acetate 9/1).
Workup
- concentrationto saturate the solution (about 25 g)
- additionis introduced
- customThe complex formed
- washthe organic fraction is washed three times with a solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- filtrationIt is filtered
- customthe solvent is evaporated at a rotary evaporator
Sources & evidence
- ORD record
- ord-48d4601de6944eb5ac68cbb22b5c2b58
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223510
Reaction notes
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