(Diethylamino)sulfur trifluoride → HCID 86600991, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[S:15][C:16]([Br:19])=[CH:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:28][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][N:10]([CH3:20])[S:11]([C:14]1[S:15][C:16]([Br:19])=[CH:17][CH:18]=1)(=[O:13])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-bromothiophene-2-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 71) (210 mg) in dichloromethane (2 mL) was added dropwise (diethylamino)sulfur trifluoride (DAST) (0.1 mL) at −70° C., After gradually warming slowly to 0° C. over 1.5 hours, an aqueous solution of saturated sodium bicarbonate was added, and the solution was extracted with ethyl acetate. After the organic layer was washed with saturated sodium chloride water and was dried with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (169 mg) was obtained as a pale yellow oily substance.
Workup
- extractionthe solution was extracted with ethyl acetate
- washAfter the organic layer was washed with saturated sodium chloride water
- dry with materialwas dried with anhydrous sodium sulfate
- customthe residue that was obtained
- customupon removing the solvent
- customby evaporation
- customwas purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-982204c5878d4e05ac3ec4b6c380befd
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07217723B2
Reaction notes
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