Water → 1-chloro-N-ethyl-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 363290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363290
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)(=[O:5])=[O:4].I[CH2:18][CH3:19].C([O-])([O-])=O.[K+].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Cl:1][CH2:2][S:3]([N:6]([CH2:18][CH3:19])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)(=[O:4])=[O:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

Produkt 1

HCID 154053651-chloro-N-ethyl-N-(4-fluoro-3-nitrophenyl)methanesulfonamideAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (5.93 g, 22.1 mmol), iodoethane (3.79 g, 24.3 mmol), tetrabutylammonium bromide (0.712 g, 2.21 mmol), and anhydrous K2CO3 (8.85 g, 64 mmol) in anhydrous dimethylformamide (40 mL) was stirred at room temperature. When the starting material had disappeared based on thin layer chromatography on silica (6 h), the reaction mixture was poured into water (200 mL) and extracted with CH2Cl2 (500 mL). The organic extract was washed with water (two times with 50 mL), dried (MgSO4), and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 1-chlorobutane and diethyl ether 100:1 v/v eluent) to give 4.68 g of the title compound of Step B as a solid melting at 80°-83° C. 1H NMR (Me2SO-d6, 400 MHz): δ 8.17 (dd,1H, J=6.75 and 2.7 Hz), 7.85 (dd,1H, J=9.4 and 3 Hz), 7.69 (dd,1H, J=11 and 9 Hz), 5.25 (s,2H), 3.83 (q,2H), 1.04 (t,3H).

Aufarbeitung

  1. customhad disappeared based on thin layer chromatography on silica (6 h)
  2. extractionextracted with CH2Cl2 (500 mL)
  3. extractionThe organic extract
  4. washwas washed with water (two times with 50 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 1-chlorobutane and diethyl ether 100:1 v/v eluent)

Quellen und Nachweise

ORD-Eintrag
ord-1747274ee54c477d9f14386e0c8cdc23
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874382

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