Diethyl Ether → HCID 12326325, compound

HRID 1199913Notes

Reaction equation

HRID 1199913 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].CCO[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].CCOCC>CCCCCC>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6871Diethyl (ethoxymethylene)malonateHCID 113572-Ethylaniline

Product 1

HCID 12326325HCID 12326325, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-ethylaniline (11.7 g) and diethyl ethoxymethylene malonate (25.0 g) were warmed together at 80° C. for one hour. After cooling, the mixture was poured with stirring into a mixture of 150 ml of ether and 75 ml of hexane. After cooling the solution in an ice bath colorless needles precipitated and were collected by filtration. There was obtained 26.7 g (95%) of the title product; tlc, Rf =0.73, silica gel, ethyl acetate:hexane (1:1).

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured
  3. temperatureAfter cooling the solution in an ice bath colorless needles
  4. customprecipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4f58cd5d9d5f40b8a9faa4db0e09d960
Source dataset
uspto-grants-1990_02
Patent number
US04904651

Reaction notes

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