Ethyl 2-chloroacetoacetate → HCID 59295389, compound

HRID 2233281Notes

Reaction equation

HRID 2233281 reaction equation
[CH3:1][C:2]1([C:8]([NH2:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[CH:12]([C:18]([CH3:20])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:16]([O:15][C:13]([C:12]1[O:9][C:8]([C:2]2([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[N:10][C:18]=1[CH3:20])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 164785Cyclohexanecarboxamide, 1-methyl-

Product 1

HCID 59295389HCID 59295389, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

25.0 g 1-Methyl-cyclohexanecarboxylic acid amide was suspended in 40 ml ethanol and warmed to 50° C. At this temperature 29.0 ml Ethyl 2-chloroacetoacetate were added and the reaction mixture heated under reflux overnight. The cooled reaction mixture was evaporated under reduced pressure and the resulting residue was purified by chromatography with the eluent petroleum ether:ethyl acetate=4:1 to obtain 21.0 g 4-Methyl-2-(1-methyl-cyclohexyl)-oxazole-5-carboxylic acid ethyl ester as an oil which solidifies upon standing.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. customwas evaporated under reduced pressure
  5. customthe resulting residue was purified by chromatography with the eluent petroleum ether

Sources & evidence

ORD record
ord-419295e9b23f46c2ad092eda61bcfde2
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

Loading…