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

HRID 363290Notes

Reaction equation

HRID 363290 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 154053651-chloro-N-ethyl-N-(4-fluoro-3-nitrophenyl)methanesulfonamideYield 71.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1747274ee54c477d9f14386e0c8cdc23
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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