Triethylamine → 4-fluoro-N-methyl-3-nitrobenzenesulfonamide

HRID 536039Notes

Reaction equation

HRID 536039 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([N:17](CC)CC)C.Cl.CN>C1COCC1.O.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][CH3:15])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 84680854-fluoro-N-methyl-3-nitrobenzenesulfonamideYield 90.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
-35 °C

Procedure

To a solution of 4-fluoro-3-nitrobenzenesulfonyl chloride (43 g, 179.5 mmol) in THF (500 mL), was added triethylamine (150 mL, 1.08 mol). The mixture was cooled to −35° C. and methylamine hydrochloride (14.5 g, 215.4 mmol) in water was added dropwise. After 1 h, the mixture was warmed to room temperature and diluted with 1:1 water/ethyl acetate. The organic layer was separated and washed with saturated aqueous sodium bicarbonate, then brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified via column chromatography (20% ethyl acetate/petroleum ether) to give 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (38 g, 90% yield) as a yellow solid.

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified via column chromatography (20% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-69cc068fb9f14d6d923830fbee6d8b96
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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