1-Propanesulfonyl chloride → Propane-1-Sulfonic Acid Cyclopropyl Amide

HRID 2177119Notes

Reaction equation

HRID 2177119 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH2:5]([S:8](Cl)(=[O:10])=[O:9])[CH2:6][CH3:7]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([NH:4][S:8]([CH2:5][CH2:6][CH3:7])(=[O:10])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 69828Cyclopropylamine

Product 1

HCID 59547736Propane-1-Sulfonic Acid Cyclopropyl AmideYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of cyclopropylamine (1.2 ml, 17.5 mmol) in 100 ml CH2Cl2 and DMAP (2.4 g, 17.5 mmol) was added dropwise a solution of propane-1-sulfonyl chloride (2.3 ml, 19.2 mmol) in 50 ml CH2Cl2. The resulting mixture was stirred at room temperature over night and diluted with 50 ml of CH2Cl2. The mixture was extracted subsequently with water, 1 M HCl, and brine, tried over Na2SO4, filtered and the solvent evaporated to obtain 2.8 g of product (oil) which was used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted subsequently with water, 1 M HCl, and brine
  2. filtrationfiltered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-e581888a30a04e50ad674946d16796a3
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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