Methanesulfonyl chloride → N-(3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-methanesulfonamide
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:24])[C:12]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1)[NH2:5].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:26]([CH3:25])(=[O:28])=[O:27])[CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[N:11]([CH3:24])[C:12]([C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([CH3:15])[CH:14]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -5 °C
Versuchsvorschrift
3-Fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (1.0 g, 3.1 mmol) [prepared as described in Example 1] was dissolved in pyridine (10 ml) and the solution was cooled to -5° C. Methanesulfonyl chloride (0.39 g, 3.4 mmol) was added and after 1 h the reaction mixture was poured into 1 M HCl/ice/water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated to dryness. The residue was crystallized from methylene chloride-methanol to give N-(3-fluoro-4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-methanesulfonamide (775 mg, 62%) as a solid, mp 165-167° C.
Aufarbeitung
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated to dryness
- customThe residue was crystallized from methylene chloride-methanol
Quellen und Nachweise
- ORD-Eintrag
- ord-6b99d7fb7bdd473d8f3c5b962f15ed53
- Quelldatensatz
- uspto-grants-1999_09
- Patentnummer
- US05952368
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