Hydrochloric Acid → HCID 43255333, compound

HRID 536051Notes

Reaction equation

HRID 536051 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].Cl.CN.[CH2:18]([N:20](CC)CC)C.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH:20][CH3:18])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 129043722-Fluoro-5-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 43255333HCID 43255333, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluoro-5-nitrobenzenesulfonyl chloride (3.2 g, 12.6 mmol) in THF (30 mL) at −45° C. was treated with methylamine hydrochloride (1.0 g, 15.1 mmol) and triethylamine (2.1 mL, 15.1 mmol) and stirred for 30 minutes. The mixture was then treated with 6M aqueous HCl to adjust the pH to 3 and warmed to room temperature before being diluted with water and extracted with EtOAc. The organic extract was dried (sodium sulfate), concentrated, and subjected to flash chromatography (5-20% EtOAc-petroleum ether) to give 2-fluoro-N-methyl-5-nitrobenzenesulfonamide as a yellow solid (3.0 g, 93%). MS (m/z) 235.1 (M+H+).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-872736042e694dc5867ee281ab6883ca
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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