Hydrochloric Acid → Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

HRID 2088669Notes

Reaction equation

HRID 2088669 reaction equation
[Na].[NH2:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[CH:4][C:5]#[N:6].[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:17]([O:16][C:15](=[O:19])[NH:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[CH:4][C:5]#[N:6])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5360545SodiumHCID 669113223-Amino-3-(2,4-dichlorophenyl)acrylonitrile

Product 1

HCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.85 g (211 mmol) of sodium were dissolved in ethanol (260 ml), 30.0 g (141 mmol) of 3-amino-3-(2,4-dichlorophenyl)acrylonitrile and 36.59 g (310 mmol) of diethyl carbonate were added and the reaction solution was stirred under reflux for 4 h. Ethyl acetate and water were added to the reaction mixture, and the pH was adjusted to pH=5 with concentrated hydrochloric acid. The organic phase was separated off, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 7:1 to 1:1), the product had an Rf=0.5 in cyclohexane/ethyl acetate 1:1. This gave 17.1 g (43% of theory) of the product.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe organic phase was separated off
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 7:1 to 1:1)

Sources & evidence

ORD record
ord-fd04a291549b4a70b876b25eb7588c8b
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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