Methanesulfonyl chloride → N-(2-methylcyclopentyl)methanesulfonamide

HRID 1776243Notes

Reaction equation

HRID 1776243 reaction equation
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH2:8].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[NH:8][S:10]([CH3:9])(=[O:12])=[O:11]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 191014392-Methylcyclopentan-1-amine hydrochloride

Product 1

HCID 63373715N-(2-methylcyclopentyl)methanesulfonamideYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-methylcyclopentanamine hydrochloride (0.100 g, 0.7 mmol) in pyridine (1 mL) was added methanesulfonyl chloride (0.095 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 16 hrs. The mixture was diluted with ethyl acetate and washed with 2 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to afford the product as a brown solid (0.100 g, 84%). The material was used without further purification.

Workup

  1. washwashed with 2 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07b1ba097b3a4592a6d654bebd0629bf
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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