Ammonia → (2E,4E)-4-ethylhexa-2,4-dienamide
Reaction equation
[CH2:1](/[C:3](=[CH:9]\[CH3:10])/[CH:4]=[CH:5]/[C:6](O)=[O:7])[CH3:2].C([N:13](CC)CC)C.ClC(OC(C)C)=O.N>ClCCl>[CH2:1](/[C:3](=[CH:9]\[CH3:10])/[CH:4]=[CH:5]/[C:6]([NH2:13])=[O:7])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 16.0 kg (114 mol) of (E,E)-4-ethyl-2,4-hexadienoic acid and 11.5 kg (114 mol) of triethylamine in 112 l of dichloromethane is added dropwise 14.0 kg (114 mol) of isopropyl chloroformate at -5°~-10° C. and the reaction is continued for 1 hour at same temperature. To this solution is introduced 7.4 kg (435 mol) of anhydrous ammonia gas and allowed to stand overnight at 20°-30° C. The solvent and excess ammonia gas is removed under reduced pressure. The residue is dissolved in 128 l of ethyl acetate and washed with 80 l of 5%-sodium chloride solution, 80 l of 5%-hydrochloric acid solution, 80 l of 5%-sodium chloride solution, 80l of 7%-sodium hydroxide solution and 80 l of 5%-sodium chloride solution respectively. The solvent is removed under reduced pressure to give 11.9 kg of (E,E)-4-ethyl-2,4 -hexadienamide as a yellow oil (Yield 74.7%).
Workup
- waitto stand overnight at 20°-30° C
- customThe solvent and excess ammonia gas is removed under reduced pressure
- dissolutionThe residue is dissolved in 128 l of ethyl acetate
- washwashed with 80 l of 5%-sodium chloride solution, 80 l of 5%-hydrochloric acid solution, 80 l of 5%-sodium chloride solution, 80l of 7%-sodium hydroxide solution and 80 l of 5%-sodium chloride solution respectively
- customThe solvent is removed under reduced pressure
Sources & evidence
- ORD record
- ord-d7e6ab348b8f426dbf62ae42356d69bf
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05254733
Reaction notes
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