Sodium Hydroxide → HCID 9944509, compound

HRID 1167243Notes

Reaction equation

HRID 1167243 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[C:4]([CH3:17])[CH:3]=1.[OH-].[Na+].Cl[C:21]([F:26])([F:25])C(O)=O>CN(C=O)C.O.C(OCC)(=O)C>[F:25][CH:21]([F:26])[O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([N:14]([CH3:16])[CH3:15])(=[O:12])=[O:13])=[C:4]([CH3:17])[CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 66154Chlorodifluoroacetic acidHCID 22996562HCID 22996562, compound

Product 1

HCID 9944509HCID 9944509, compoundYield 21.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-hydroxy-2-methyl-5-nitro(N,N-dimethyl)benzenesulfonamide (200 mg, 0.77 mmol) in dry DMF (2 mL) was added sodium hydroxide (74 mg, 1.85 mmol) and chlorodifluoroacetic acid (120 mg, 0.92 mmol). The resulting reaction mixture was stirred at 120° C. for 18 h. After cooling, the reaction was diluted with water and ethyl acetate, and the layers were separated. The organics were washed three times with 1 N NaOH, dried and concentrated. The residue was purified by flash chromatography (20% ethyl acetate/hexanes) to provide 4-difluoromethoxy-2-methyl-5-nitro (N,N-dimethyl)-benzenesulfonamide (51 mg, 21%) as a yellow solid, mp 125-126° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. customthe layers were separated
  4. washThe organics were washed three times with 1 N NaOH
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-942531d4e5d643aba7888b09e059e6a5
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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