Diphenylacetonitrile → HCID 178510933, compound

HRID 1278467Notes

Reaction equation

HRID 1278467 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1>CN(C)C=O>[NH:24]1[CH:25]=[C:21]([CH2:20][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:8]#[N:9])[N:22]=[CH:23]1

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 178478565HCID 178478565, compound

Product 1

HCID 178510933HCID 178510933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 5.80 g. portion of diphenylacetonitrile and 1.5 g. of 50% sodium hydride were reacted for 30 minutes in 20 ml. of dimethylformamide, and 2.29 g. of 4-chloromethylimidazole hydrochloride in 20 ml. of dimethylformamide was added. The reaction mixture was stirred at ambient temperature for about 15 minutes, the solvent was evaporated from the mixture under vacuum, and the residue was worked up as described in Example 1 to obtain 3.0 g. of the desired product as the free base, which was identified by 60 mHz nuclear magnetic resonance analysis in CDCl3, showing the following characteristic peaks: δ9.05 (broad m, 1H); 7.32 (m, 11H); 6.60 (s, 1H); 3.68 (s, 2H).

Workup

  1. customthe solvent was evaporated from the mixture under vacuum
  2. customto obtain 3.0 g

Sources & evidence

ORD record
ord-f658e7c2a65c48b68aff8278f3b71332
Source dataset
uspto-grants-1981_07
Patent number
US04281141

Reaction notes

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