Diethyl Ether → HCID 178500762, compound

HRID 255632Notes

Reaction equation

HRID 255632 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[F:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.[CH2:25](OCC)C>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10](=[O:16])[C:11](=[CH:25][NH:22][C:21]2[CH:23]=[CH:24][C:18]([F:17])=[CH:19][CH:20]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 97314-FluoroanilineHCID 53683143HCID 53683143, compound

Product 1

HCID 178500762HCID 178500762, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 10 ml of benzene was dissolved 2.0 g of methyl 5-(4-chlorophenyl)-3-oxo-4-pentenoate, and to this solution was added 1.2 g of N,N-dimethylformamidodimethylacetal. The resulting mixture was subjected to reaction at 70° C. for 1.5 hours. The reaction mixture was cooled to room temperature, and 1.12 g of p-fluoroaniline was then added thereto, after which the resulting mixture was further subjected to reaction for 1.5 hours. After completion of the reaction, 10 ml of diethyl ether was added to the reaction mixture, and the precipitated crystals were collected by filtration, and washed with 10 ml of diethyl ether to obtain 2.2 g of methyl 5-(4-chlorophenyl)-2-(4-fluorophenylaminomethylene)-3-oxo-4-pentenoate having a melting point of 166°-168° C.

Workup

  1. customThe resulting mixture was subjected to reaction at 70° C. for 1.5 hours
  2. customafter which the resulting mixture was further subjected to reaction for 1.5 hours
  3. additionwas added to the reaction mixture
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with 10 ml of diethyl ether

Sources & evidence

ORD record
ord-0341fc067cb1449bbb5d2e7d0f10558c
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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