Hydrochloric Acid → 2-Fluoro-N-methyl-5-nitro-4-(2,2,2-trifluoroethoxy)benzenesulfonamide

HRID 536058Notes

Reaction equation

HRID 536058 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[S:17](Cl)(=[O:19])=[O:18].Cl.CN.[CH2:24]([N:26](CC)CC)C.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[S:17]([NH:26][CH3:24])(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 43247009HCID 43247009, compound

Product 1

HCID 671692982-Fluoro-N-methyl-5-nitro-4-(2,2,2-trifluoroethoxy)benzenesulfonamideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

A mixture of 2-fluoro-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonyl chloride (15 g, crude) in THF (150 mL) at −45° C. was treated with methylamine hydrochloride (5.96 g, 89 mmol) and then treated dropwise with triethylamine (12.4 mL, 89 mmol). After stirring for 1 hour at −45° C., the mixture was adjusted to pH 3 by the addition of aqueous 3M HCl, warmed to room temperature, diluted with water, and extracted with EtOAc. The organic extract was dried (Na2SO4), concentrated, and subjected to flash chromatography (9-17% EtOAc-petroleum ether) to give 2-fluoro-N-methyl-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzenesulfonamide (10 g, 72% for two steps) as a yellow solid. MS (m/z) 333.0 (M+H+).

Workup

  1. temperaturewarmed to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-326d7a5b2fa4456495ddf0353e66c6ff
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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