ethyl 2-(N-methyleneamino)-2-methylpropanoate → ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoate

HRID 1003154Notes

Reaction equation

HRID 1003154 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]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>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]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][O:12][C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 10855576ethyl 2-(N-methyleneamino)-2-methylpropanoateHCID 153008465-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one

Product 1

HCID 86755276ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoateYield 62.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 5-(2-fluorophenyl)-2,2-dimethyl-6-methyl-4H-1,3-dioxin-4-one (2.0 g) and ethyl 2-(N-methyleneamino)-2-methylpropionate (1.45 g) was heated under reflux in xylene for 10 hours. After evaporation to dryness the residue was purified by dry column chromatography on silica gel eluting with cyclohexane/ethyl acetate to give ethyl [5-(2-fluorophenyl)-2,3-dihydro-6-methyl-4-oxo-4H-1,3-oxazin-3-yl]-2-methylpropanoate as a pale yellow oil (1.7 g), NMR 1.24(t,3H), 1.42(s,6H), 1.57(s,3H), 4.15(q,2H), 5.3(s,2H), 7. 74(m,4H).

Workup

  1. temperaturewas heated
  2. customAfter evaporation to dryness the residue
  3. customwas purified
  4. dry with materialby dry column chromatography on silica gel eluting with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-086c87bfb705496487e718d7a6ebca51
Source dataset
uspto-grants-2000_04
Patent number
US06046135

Reaction notes

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