2-Phenylpropionitrile → HCID 178457096, compound

HRID 1278471Notes

Reaction equation

HRID 1278471 reaction equation
[C:1]1([CH:7]([CH3:10])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl[CH2:15][C:16]1[N:17]=[CH:18][NH:19][CH:20]=1>CN(C)C=O>[NH:19]1[CH:20]=[C:16]([CH2:15][C:7]([CH3:10])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]#[N:9])[N:17]=[CH:18]1

Participants

5

Reactant 3

HCID 157612-PhenylpropionitrileHCID 24758Sodium hydrideHCID 178478565HCID 178478565, compound

Product 1

HCID 178457096HCID 178457096, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

As described in Example 1, 5.82 g. of 2-phenylpropanenitrile, 2.04 g. of 50% sodium hydride, and 3.06 g. of 4-chloromethylimidazole hydrochloride were reacted in 40 ml. of dimethylformamide. The mixture was stirred for 5 hours at 100° C., and for 16 hours at ambient temperature. The solvent was then evaporated away under vacuum, and the residue was worked up as described in Example 1 to obtain 0.4 g. of crude free base. The product was purified by preparative thin layer chromatography on silica gel with ethyl acetate as the eluant. The purified product was converted to 0.11 g. of the hydrochloride salt of the desired product, m.p. 187°-189° C.

Workup

  1. waitfor 16 hours at ambient temperature
  2. customThe solvent was then evaporated away under vacuum
  3. customto obtain 0.4 g
  4. customThe product was purified by preparative thin layer chromatography on silica gel with ethyl acetate as the eluant

Sources & evidence

ORD record
ord-c62be30d7e5e4adbaf294f4491810c2d
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

Loading…