Isopropylamine → n-isopropylbenzenesulfonamide

HRID 660649Notes

Reaction equation

HRID 660649 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[C:5]1([S:11](Cl)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[CH:1]([NH:4][S:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:13])=[O:12])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 7369Benzenesulfonyl chloride

Product 1

HCID 220600n-isopropylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropylamine (4.2 g, 70.6 mmol) in methylene chloride (50 mL) at 0-5° C. is added dropwise a solution of benzenesulfonyl chloride (5.0 g, 28.3 mmol) in methylene chloride (10 mL). After stirring the mixture at RT for 2 h, the solvent is removed under reduced pressure and 1N HCl is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine then dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound as a pale yellow oil.

Workup

  1. customthe solvent is removed under reduced pressure and 1N HCl
  2. additionis added to the residue
  3. extractionThe mixture is extracted with EtOAc
  4. washthe organic phase is washed with brine
  5. dry with materialthen dried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5d62cb63b62440f98ae24ed602102b5a
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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