N-methylene-1-methyl-1-(3-chlorophenyl)ethylamine → 5-isobutyl-6-methyl-3-[1-methyl-1-(3-chlorophenyl)ethyl]-2,3-dihydro-4H-1,3-oxazin-4-one

HRID 1648194Notes

Reaction equation

HRID 1648194 reaction equation
[CH2:1]([C:5]1[C:6](=[O:14])O[C:8](C)(C)[O:9][C:10]=1[CH3:11])[CH:2]([CH3:4])[CH3:3].C=[N:16][C:17]([CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[CH3:18]>C1(C)C(C)=CC=CC=1>[CH2:1]([C:5]1[C:6](=[O:14])[N:16]([C:17]([CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:18])[CH2:8][O:9][C:10]=1[CH3:11])[CH:2]([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 15300847N-methylene-1-methyl-1-(3-chlorophenyl)ethylamineHCID 199189545-isobutyl-2,2,6-trimethyl-2H,4H-1,3-dioxin-4-one

Product 1

HCID 199189625-isobutyl-6-methyl-3-[1-methyl-1-(3-chlorophenyl)ethyl]-2,3-dihydro-4H-1,3-oxazin-4-oneYield 54.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Xylene (1 ml) was added to a mixture of 5-isobutyl-2,2,6-trimethyl-2H,4H-1,3-dioxin-4-one (0.59 g) and N-methylene-1-methyl-1-(3-chlorophenyl)ethylamine (0.55 g), and the resulting mixture was heated at reflux for 60 minutes for reaction. The reaction mixture was purified by silica gel chromatography to obtain the captioned compound (0.52 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 60 minutes for reaction
  3. customThe reaction mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-116adac64a8a438e812a14abc08bb7f8
Source dataset
uspto-grants-1995_07
Patent number
US05436224

Reaction notes

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