Chlorosuccinimide → HCID 86597492, compound
Reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:11]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][S:13][CH:14]=1>C(O)(=O)C>[Cl:1][C:12]1[S:13][CH:14]=[C:10]([CH3:9])[C:11]=1[NH:15][C:16](=[O:21])[C:17]([F:20])([F:18])[F:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 3.2 g of N-chlorosuccinimide in 50 ml of glacial acetic acid was added dropwise to a mixture of 5 g of 4-methyl-3-trifluoroacetylaminothiophene in 70 ml of glacial acetic acid, and the mixture was then stirred at room temperature for 30 minutes and at 50° C. for a further hour. The solvent was distilled off, and the residue was admixed with water and adjusted to pH 10 using 2N NaOH. The mixture was extracted using ethyl acetate, and the organic phase was washed with water and dried over sodium sulfate. After the solvent had been distilled off, a dark-colored oily product was obtained and was chromatographically purified on silica gel using an elution mixture of 10 parts by volume of toluene and 2 parts by volume of n-heptane. After the solvent had been distilled off, the product was obtained as a light yellow-colored oil.
Workup
- distillationThe solvent was distilled off
- extractionThe mixture was extracted
- washthe organic phase was washed with water
- dry with materialdried over sodium sulfate
- distillationAfter the solvent had been distilled off
- customa dark-colored oily product was obtained
- customwas chromatographically purified on silica gel using
- additionan elution mixture of 10 parts by volume of toluene and 2 parts by volume of n-heptane
- distillationAfter the solvent had been distilled off
- customthe product was obtained as a light yellow-colored oil
Sources & evidence
- ORD record
- ord-f22e9d4a64324789b19dacdd7a3f9c1e
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179830B2
Reaction notes
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