Allyl chloride → 2,6-Di(propan-2-yl)-N-(prop-2-en-1-yl)aniline

HRID 2250974Notes

Reaction equation

HRID 2250974 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[CH2:14](Cl)[CH:15]=[CH2:16].[OH-].[Na+]>O>[CH2:16]([NH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 32484Diisopropylaniline

Product 1

HCID 713595712,6-Di(propan-2-yl)-N-(prop-2-en-1-yl)anilineYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution containing 2,6-diisopropyl aniline (35.4 g, 0.2 mol) and allyl chloride (7.6 g, 0.10 mol) was refluxed for 12 hr and then poured into water (400 ml). Adding an aqueous NaOH solution to the reaction mixture made the mixture basic. After extraction with diethyl ether (3×50 ml) and distillation (73.25 Pa, 92° C.), 18.33 g (84.3%) of N-allyl-2,6-diisopropyl aniline was isolated. Nd30=1.5205. 1H-NMR (ppm,CDCl3): δ=7.10(d, 2H, Ph-Hm), 6.81(t, 1H, Ph-Hp), 6.05(m, 1H, CH═C), 5.34(d, 1H, C═C—Htrans), 5.16(d, 1H, C═C—Hcis), 3.71(broad, 1H, NH), 3.50(d, 2H, CH2—C═C), 3.26(m, 2H, CH(Me)2), 1.28(d, 12H, C═C(CH3)2).

Workup

  1. temperaturewas refluxed for 12 hr
  2. extractionAfter extraction
  3. distillationwith diethyl ether (3×50 ml) and distillation (73.25 Pa, 92° C.)

Sources & evidence

ORD record
ord-9c62d49983df43f1b0c17e32ec0081be
Source dataset
uspto-grants-2008_01
Patent number
US07319083B2

Reaction notes

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