Hydrochloric Acid → N-Butyl-p-toluenesulfonamide

HRID 1647693Notes

Reaction equation

HRID 1647693 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[C:6]1([CH3:16])[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.Cl>C(Cl)Cl.[OH-].[Na+]>[CH2:1]([NH:5][S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:16])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8007Butylamine

Product 1

HCID 61285N-Butyl-p-toluenesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve butylamine (10 mmol) in methylene chloride (50 mL) and 10% sodium hydroxide (50 mL). Cool to 0° C. Add excess p-toluenesulfonyl chloride with stirring. After 1 hour allow the reaction to warm to room temperature and stir for 2 days. Neutralize the reaction with 0.5N hydrochloric acid and extract the aqueous with methylene chloride (2×100 mL). Rinse the combined organic extracts with water (100 mL), brine (100 mL), dry over anhydrous sodium sulfate, filter and concentrate under vacuum to provide N-butyl-4-methyl-benzenesulfonamide.

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. extractionextract the aqueous with methylene chloride (2×100 mL)
  4. washRinse the combined organic extracts with water (100 mL), brine (100 mL)
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-a21399b85c3940318e83ae94183ab394
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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