Methanesulfonyl chloride → HCID 86702163, compound

HRID 1776241Notes

Reaction equation

HRID 1776241 reaction equation
Cl.[CH3:2][C:3]1([NH2:6])[CH2:5][CH2:4]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:2][C:3]1([NH:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12953687(1-Methylcyclopropyl)amine hydrochloride

Product 1

HCID 86702163HCID 86702163, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-methylcyclopropan-1-amine hydrochloride (0.100 g, 0.9 mmol) in pyridine (1 mL) was added methanesulfonyl chloride (0.108 mL, 1.4 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 yellow oil (0.105 g, 76%). 1H NMR (300 MHz, CDCl3) δ 4.68 (br s, 1H), 3.02 (s, 3H), 1.50 (s, 3H), 1.02-0.94 (m, 2H), 0.71-0.64 (m, 2H).

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-2f88ab55818f444392c338762d4ef447
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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