Sodium Hydroxide → 4-Amino-2-fluoro-N-methylbenzenesulfonamide

HRID 1959789Notes

Reaction equation

HRID 1959789 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:13]C(=O)C)[CH:5]=[CH:6][C:7]=1[S:8](=[O:12])(=[O:11])[NH:9][CH3:10].[OH-].[Na+]>Cl>[NH2:13][C:4]1[CH:5]=[CH:6][C:7]([S:8]([NH:9][CH3:10])(=[O:12])=[O:11])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 34029456N-(3-fluoro-4-methylsulfamoylphenyl)acetamide

Product 1

HCID 617181244-Amino-2-fluoro-N-methylbenzenesulfonamideYield 83.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The above prepared N-(3-fluoro-4-methylsulfamoylphenyl)acetamide (1.55 g, 6.3 mmol) was suspended in 40 mL of 6M HCl and heated to reflux for 1 hr. The reaction was cooled in an ice bath and an NaOH solution was added to adjust the mixture to pH 5. The resulting white precipitate was isolated by filtration and was washed with water and dried to yield 1.07 g (83%) of the title compound. MS (m/z, ES+): 205.0 (M+1, 100%); 1H NMR (500 MHz, ppm, DMSO-d6): 7.35 (m, 1H), 7.12 (m, 1H), 6.40 (m, 2H), 6.23 (s, 2H), 2.40 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hr
  3. temperatureThe reaction was cooled in an ice bath
  4. customThe resulting white precipitate was isolated by filtration
  5. washwas washed with water
  6. customdried

Sources & evidence

ORD record
ord-b65f65d5a77643a7b028dbaf86d32040
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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