5-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one → 5-(2-fluorophenyl)-6-methyl-3-[1-methyl-1-(3-chlorophenyl)ethyl]-2,3-dihydro-4H-1,3-oxazin-4-one

HRID 1648191Notes

Reaction equation

HRID 1648191 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:17])O[C:11](C)(C)[O:12][C:13]=1[CH3:14].C=[N:19][C:20]([CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH3:21]>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:17])[N:19]([C:20]([CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH3:21])[CH2:11][O:12][C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 153008465-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one2×HCID 15300847N-methylene-1-methyl-1-(3-chlorophenyl)ethylamine2×

Product 1

HCID 153008485-(2-fluorophenyl)-6-methyl-3-[1-methyl-1-(3-chlorophenyl)ethyl]-2,3-dihydro-4H-1,3-oxazin-4-oneYield 83.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Xylene (2 ml ) was added to a mixture of 5-(2-fluorophenyl)-2,2 ,6-trimethyl-2H,4H-1,3-dioxin-4-one (compound of Example 1 ) (0.71 g) and N-methylene-1-methyl1-(3-chlorophenyl)ethylamine (compound of Example 3) (0.6 g), and the resulting mixture was heated at reflux for 20 minutes for reaction. The reaction mixture was purified by silica gel chromatography to obtain the captioned compound (0.9 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 20 minutes for reaction
  3. customThe reaction mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-026a776b6c0e4b20909da49e783b63d8
Source dataset
uspto-grants-1995_07
Patent number
US05436224

Reaction notes

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