Ethyl cyanoacetate → (E)-ethyl 3-aMino-4,4,4-trichloro-2-isocyanobut-2-enoate
Reaction equation
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].[CH2:7]([O:9][C:10](=[O:14])[CH2:11][C:12]#[N:13])[CH3:8]>C(O)C.C(N(CC)CC)C>[NH2:4]/[C:3](/[C:2]([Cl:6])([Cl:5])[Cl:1])=[C:11](/[C:12]#[N:13])\[C:10]([O:9][CH2:7][CH3:8])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of trichloroacetonitrile (38 mL, 0.38 mol) and cyanoacetic acid ethyl ester (20 mL, 0.2 mol) in ethanol (63 mL) was added triethylamine (1 mL, 7 mmol). The reaction mixture began to turn red and an exotherm occurred after ˜1 minute. The reaction mixture was cooled to 0° C., then stirred for two hours while slowly warming to room temperature. The reaction mixture was concentrated in vacuo to a red oil, which was taken up in DCM, filtered through a plug of silica gel, and concentrated in vacuo to afford 44.95 g (90%) of (Z)-ethyl 3-amino-4,4,4-trichloro-2-cyanobut-2-enoate as a colorless oil that slowly solidified to a white solid. 1H NMR (400 MHz, CDCl3) δ 10.19 (s, 1H), 6.85 (s, 1H), 4.31 (q, J=7.1, 1H), 1.37 (t, J=7.1, 3H).
Workup
- temperaturewhile slowly warming to room temperature
- concentrationThe reaction mixture was concentrated in vacuo to a red oil, which
- filtrationfiltered through a plug of silica gel
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-48167abcd40a4e62ab626946a7adec0d
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999998B2
Reaction notes
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