Allylamine → 15411-32-2

HRID 1776234Notes

Reaction equation

HRID 1776234 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(N(CC)CC)C.Cl[CH2:13][CH2:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH2:1]([NH:4][S:15]([CH:14]=[CH2:13])(=[O:17])=[O:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-

Product 1

HCID 2046268215411-32-2

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled, 0° C., solution of allylamine (1.926 g, 33.7 mmol) and triethylamine (12.789 mL, 92.0 mmol) in anhydrous methylene chloride (50 mL) was slowly added a solution of 2-chloroethanesulfonyl chloride (5.000 g, 30.7 mmol) in methylene chloride (10 mL). The resulting mixture was allowed to warm to room temperature and stirred for 4 hrs. The mixture was successively extracted with 1 N aqueous hydrochloric acid (2×), water, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to give a yellow liquid. 1H NMR (300 MHz, CDCl3) δ 6.57-6.48 (dd, 1H, J=9.9, 16.8 Hz), 6.28-6.22 (d, 1H, J=16.8 Hz), 5.96-5.92 (d, 1H, J=9.6 Hz), 5.90-5.77 (m, 1H), 5.30-5.29 (m, 1H), 5.24-5.17 (m, 1H), 4.44 (br s, 1H), 3.69-3.64 (tt, 2H, J=1.5, 6.0 Hz).

Workup

  1. extractionThe mixture was successively extracted with 1 N aqueous hydrochloric acid (2×), water, saturated aqueous sodium chloride
  2. dry with materialdried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a yellow liquid

Sources & evidence

ORD record
ord-7eedf6abc679442ebf01dd81e0494fad
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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