Acetic Acid → Ethyl 2-cyano-3-(5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-phenyl)-propenoate

HRID 1719652Notes

Reaction equation

HRID 1719652 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH:10]=O.[C:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[C:25]([C:27](=[CH:10][C:9]1[CH:12]=[C:5]([O:4][C:3]2[C:2]([Cl:1])=[CH:19][C:18]([C:20]([F:23])([F:21])[F:22])=[CH:17][C:16]=2[Cl:24])[CH:6]=[CH:7][C:8]=1[N+:13]([O-:15])=[O:14])[C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 13050449HCID 13050449, compound

Product 1

HCID 70481689Ethyl 2-cyano-3-(5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-phenyl)-propenoateYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

19 g of 5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-benzaldehyde, 5.7 g of ethyl cyanoacetate, 0.6 g of acetic acid, 0.3 g of piperidine and 120 ml of toluene were mixed and heated to the boil for 6 hours under a water separator. 200 ml of toluene was then added and the organic phase was washed with water. The solvent was distilled from the organic phase and the residue was caused to crystallise by digestion with methanol. 12.5 g (53% of theory) of ethyl 2-cyano-3-(5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-phenyl)-propenoate, of melting point 99° C., were obtained in the form of pale yellow crystals.

Workup

  1. temperatureheated to the boil for 6 hours under a water separator
  2. washthe organic phase was washed with water
  3. distillationThe solvent was distilled from the organic phase
  4. customto crystallise by digestion with methanol

Sources & evidence

ORD record
ord-15b4a56093604fb1bc6c277915291f70
Source dataset
uspto-grants-1985_09
Patent number
US04540827

Reaction notes

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