Pyridine → HCID 54471283, compound

HRID 233286Notes

Reaction equation

HRID 233286 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:24])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=2)[N:12]=1.[C:25]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26].N1CCCCC1.N1C=CC=CC=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:24])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:23]=[CH:22][C:19]([CH:20]=[C:27]([C:25]#[N:26])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18][CH:17]=2)[N:12]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 10991479Benzaldehyde, 4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]-

Product 1

HCID 54471283HCID 54471283, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]benzaldehyde (2.0 g), ethyl cyanoacetate (0.795 g), piperidine (0.15 g) and pyridine (30 ml) was stirred for 2 hours at 100°-110° C. The reaction mixture was poured into water. Resulting crystalline precipitate was collected by filtration and recrystallized from dichloromethane-ethanol to give ethyl 4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]-α-cyanocinnamate (2.45 g, 96%) as colorless needles, m.p.120°-121° C.

Workup

  1. filtrationResulting crystalline precipitate was collected by filtration
  2. customrecrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-4fd84f3a4204497a93df2c2c964b1741
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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