Aniline → HCID 22121642, compound

HRID 1590235Notes

Reaction equation

HRID 1590235 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])[CH:9]=[CH2:10].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:2]1([NH:1][CH2:10][CH2:9][C:8]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 15458tert-Butyl acrylateHCID 24287Tin tetrachloride

Product 1

HCID 22121642HCID 22121642, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of aniline (27.9 g, 0.30 mol) and tert-butyl acrylate (38.4 g, 0.30 mol) in dry benzene (500 ml) was added tin tetrachloride (2 ml) and the resulting solution was heated under reflux for 18 h. The resulting suspension was filtered and the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane to give the title compound (22.53 g, 34%) as an oil. 1H NMR (300 MHz, CDCl3) δ7.12 (2H, t), 6.71 (1H, m), 6.62 (2H, d), 3.40 (2H, t), 2 54 (2H, t), 1.44 (9H, s).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 18 h
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customgiving a residue which
  6. customwas chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane

Sources & evidence

ORD record
ord-efec110744b1461a909936272d99ecc3
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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