Potassium Carbonate → N-(4-amino-2,6-dimethylphenyl)-4-methylbenzenesulfonamide

HRID 905581Notes

Reaction equation

HRID 905581 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[C:13]([CH2:20]C)[C:12]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])C.C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[NH2:17][C:15]1[CH:14]=[C:13]([CH3:20])[C:12]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[C:11]([CH3:9])[CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 155515Benzenesulfonamide, N-(2,6-diethyl-4-nitrophenyl)-4-methyl-

Product 1

HCID 678161N-(4-amino-2,6-dimethylphenyl)-4-methylbenzenesulfonamideYield 27.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of sodium dithionite (772 mg) in water (6 mL) was added to a solution of N-(2,6-diethyl-4-nitro-phenyl)-4-methyl-benzenesulfonamide (309 mg) in tetrahydrofuran (6 mL) and the resulting mixture was stirred at 50° C. for 20 hours. After cooling, the water was saturated with potassium carbonate and extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 70 mg (25%) of the title compound as a off-white solid. The product was used directly in the following reaction without spectral characterization.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-392b47f77c9c4afb81da99df8b17c224
Source dataset
uspto-grants-2011_09
Patent number
US08012962B2

Reaction notes

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