4-(Methylthio)aniline → Propane-2-sulfonic acid (4-methylsulfanyl-phenyl)-amide

HRID 857287Notes

Reaction equation

HRID 857287 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:10]([S:13](Cl)(=[O:15])=[O:14])([CH3:12])[CH3:11]>N1C=CC=CC=1.Cl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:13]([CH:10]([CH3:12])[CH3:11])(=[O:15])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 660384-(Methylthio)anilineHCID 824082-Propanesulfonyl chloride

Product 1

HCID 25044559Propane-2-sulfonic acid (4-methylsulfanyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

To solution of 4-methylsulfanyl-phenylamine (1.1 eq) in pyridine (1.3M) at 0° C. was added iso-propylsulfonyl chloride (1.5 eq). The mixture was stirred at room temperature for 12 h, poured in HCl (1N) and extracted with EtOAc. The combined organic extracts were washed with HCl (1N; 2×), water (2×), brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc 0 to 50% in 15 min) and a suspension-filtration sequence in Hex/CH2Cl2 afforded the desired compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with HCl (1N; 2×), water (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6a3c70aacb5d4a8399c4371d0c88f36e
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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