Water → 4-fluoro-2-[N-methyl-N-(2,2,2-trifluoroacetyl)aminomethyl]benzenesulfonyl chloride
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]([CH3:13])[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[Cl:17][S:18](O)(=[O:20])=[O:19].O>ClCCCl>[F:1][C:2]1[CH:16]=[CH:15][C:14]([S:18]([Cl:17])(=[O:20])=[O:19])=[C:4]([CH2:5][N:6]([CH3:13])[C:7](=[O:12])[C:8]([F:10])([F:11])[F:9])[CH:3]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A solution of 3-fluoro-N-methyl-N-(trifluoroacetyl)benzylamine (Intermediate 159, 0.497 g) in DCE (0.5 mL) was added to stirred, cooled chlorosulfonic acid (3 mL). The mixture was allowed to come up to room temperature and then heated at 70° C. for 3 hours. After cooling, the mixture was added carefully to a mixture of ice and water, then extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane with a gradient of 2.5-10% to give 4-fluoro-2-[N-methyl-N-(2,2,2-trifluoroacetyl)aminomethyl]-benzenesulfonyl chloride (0.21 g) as a clear oil.
Aufarbeitung
- customto come up to room temperature
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washwashed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was purified by chromatography on silica
- washeluting with a mixture of ethyl acetate and pentane with a gradient of 2.5-10%
Quellen und Nachweise
- ORD-Eintrag
- ord-cf5786486b444d1682152ce7cdb8fa3f
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09290472B2
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