Aniline → HCID 22910075, compound

HRID 847586Notes

Reaction equation

HRID 847586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([CH:10]1[O:12][CH2:11]1)Cl.[OH-].[Na+]>CN(C)C=O>[OH:12][CH:10]([CH2:11][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:8][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 22910075HCID 22910075, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 0.25 ml (2.74 mmol) of aniline, 0.107 ml (1.37 mmol) of epichlorohydrin, and 60.4 mg (1.51 mmol) of sodium hydroxide in 2 ml of dimethylformamide was heated at 110° C. for 20 h. The solvent was removed in vacuo and the residue was purified by flash chromatography using 5% ethyl acetate in chloroform to give 21 mg (6%) of the desired compound (Rf 0.63, 40% ethyl acetate in chloroform). 1H NMR (CDCl3) 3.21 (dd, J=13, 8 Hz, 2H), 3.37 (dd, J=13, 4 Hz, 2H), 4.13 (m, 1H), 6.65-6.8 (m, 6H), 7.15-7.3 (m, 6H). Mass spectrum (M+H)+ =243.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d0e044b26247489ebfde125b4753cabf
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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