Ethanesulfonylchloride, 2-chloro- → HCID 86702164, compound

HRID 1776244Notes

Reaction equation

HRID 1776244 reaction equation
[CH3:1][C:2](=[CH2:5])[CH2:3][NH2:4].C(N(CC)C(C)C)(C)C.Cl[CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:5][C:2](=[CH2:1])[CH2:3][NH:4][S:18]([CH:17]=[CH2:16])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 761412-MethylallylamineHCID 81531Diisopropylethylamine

Product 1

HCID 86702164HCID 86702164, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-methylprop-2-en-1-amine (0.500 g, 7.0 mmol), N,N-diisopropylethylamine (3.486 mL, 21.1 mmol) and N,N-4-dimethylaminopyridine (0.043 g, 0.4 mmol) in methylene chloride (20 mL) at 0° C. was slowly added 2-chloroethanesulfonyl chloride (0.734 mL, 7.0 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 16 hrs. The mixture was concentrated and the residue purified by silica gel chromatography (0-80% ethyl acetate/hexanes) to afford the product as a colorless oil (0.59 g, 52%). 1H NMR (300 MHz, CDCl3) δ 6.54 (dd, 1H, J=16.5, 9.6 Hz), 6.27 (d, 1H, J=16.5 Hz), 5.96 (d, 1H, J=9.6 Hz), 4.97 (s, 1H), 4.93 (s, 1H), 4.37 (br s, 1H), 3.60 (d, 2H, J=6.3 Hz), 1.79 (s, 3H).

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by silica gel chromatography (0-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-739c5e71f62249ffaba44eeb895119c4
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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