Methanesulfonyl chloride → HCID 86702162, compound

HRID 1776240Notes

Reaction equation

HRID 1776240 reaction equation
Cl.[CH3:2][C:3]1([NH2:7])[CH2:6][CH2:5][CH2:4]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10]>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:2][C:3]1([NH:7][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 183324491-Methylcyclobutan-1-amine hydrochloride

Product 1

HCID 86702162HCID 86702162, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-methyl-cyclobutylamine hydrochloride (0.100 g, 0.8 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 oil (0.090 g, 67%). 1H NMR (300 MHz, CDCl3) δ 4.49 (br s, 1H), 3.03 (s, 3H), 2.40-2.25 (m, 2H), 2.12-2.00 (m, 2H), 1.95-1.75 (m, 2H), 1.58 (s, 3H).

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-3e9f80deddf24a7a91742f0380898da1
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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