Potassium Carbonate → Benzenesulfonamide, N-(4-amino-2,6-diethylphenyl)-4-methyl-

HRID 1867297Notes

Reaction equation

HRID 1867297 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][CH3:21])[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])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1>[NH2:17][C:15]1[CH:16]=[C:11]([CH2:9][CH3:10])[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:13]([CH2:20][CH3:21])[CH:14]=1

Participants

6

Reactant 3

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

Product 1

HCID 183982Benzenesulfonamide, N-(4-amino-2,6-diethylphenyl)-4-methyl-Yield 25%

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-f4706093401c43cc9e78aaae77ab876b
Source dataset
uspto-grants-2009_12
Patent number
US07632835B2

Reaction notes

Loading…