Phosgene → (2Z)-3-Amino-2-cyano-4-ethyl-2-hexenoyl chloride

HRID 2262447Notes

Reaction equation

HRID 2262447 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[NH2:5][C:6]([CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:7]([C:9]#[N:10])C>C1(C)C=CC=CC=1>[NH2:5]/[C:6](/[CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:7](/[C:9]#[N:10])\[C:1]([Cl:4])=[O:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 573582353-Amino-4-ethyl-2-methylhex-2-enenitrile

Product 1

HCID 86595835(2Z)-3-Amino-2-cyano-4-ethyl-2-hexenoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

250 ml toluene were cooled to 0° C. and 40 g (0.4 mol) of phosgene were added. After warming up to 25° C., 13.8 g (0.1 mol) of 3-amino-2-cyano-4-ethyl-2-hexene in toluene were added. The reaction mixture was heated at 70° C. for 4 h, then the unreacted phosgene was removed by blowing out with dry N2. After cooling to 25° C. the product precipitated. Filtration and washing with diethyl ether gave 12 g (60% of theory) of the title compound as a yellow solid (m. p. 102° C.).

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 4 h
  2. customthe unreacted phosgene was removed
  3. temperatureAfter cooling to 25° C. the product
  4. customprecipitated
  5. filtrationFiltration
  6. washwashing with diethyl ether

Sources & evidence

ORD record
ord-26d3f2a9d7d74954bc3dda81b1fafb7c
Source dataset
uspto-grants-2010_12
Patent number
US07851411B2

Reaction notes

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